[(8R,9S,10S,13S,14R,15S,17R)-10,13-二甲基-17-[(2R)-6-甲基庚烷-2-基]-2,3,4,7,8,9,11,12,14,15,16,17-十二氢-1H-环戊并[a]菲-15-基]4-氯丁酸酯 | 73112-99-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 中文名称: [(8R,9S,10S,13S,14R,15S,17R)-10,13-二甲基-17-[(2R)-6-甲基庚烷-2-基]-2,3,4,7,8,9,11,12,14,15,16,17-十二氢-1H-环戊并[a]菲-15-基]4-氯丁酸酯
• 英文名称: cholesteryl 4-chlorobutanoate
• 英文别名: Cholest-5-en-3-ol (3beta)-, 4-chlorobutanoate；[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] 4-chlorobutanoate
• CAS: 73112-99-9
• 化学式: C₃₁H₅₁ClO₂
• 分子量: 491.198
• InChiKey: FWOCLQPBUVEXDS-GTPODGLVSA-N

物化性质

• 沸点：
  549.6±33.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [(8R,9S,10S,13S,14R,15S,17R)-10,13-二甲基-17-[(2R)-6-甲基庚烷-2-基]-2,3,4,7,8,9,11,12,14,15,16,17-十二氢-1H-环戊并[a]菲-15-基]4-氯丁酸酯 在 三乙烯二胺 、 tetrakis(actonitrile)copper(I) hexafluorophosphate 、 叠氮基三甲基硅烷 、 (3aS,3aS,8aR,8aR)-2,2-(1,3-双(4-(叔丁基)苯基)丙烷-2,2-二基)双(3a,8a-二氢-8H-茚并[1,2-d]恶唑) 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 54.0h， 生成 (3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl 4-(4-(5-ethynyl-1,3-dimethyl-5H-5λ⁴,6λ⁴-pyrrolo[1',2':3,4][1,3,2]diazaborolo[1,5-a]pyridin-5-yl)-1H-1,2,3-triazol-1-yl)butanoate
  参考文献：
  名称：

  手性硼立体化合物的催化对映选择性构建

  摘要：

  主族杂原子-立体化合物的构建具有重要意义，因为它们具有有趣的化学、物理、生物和立体电子特性。尽管有机硼化合物广泛用于有机化学，但以一种对映体形式创建四面体硼立体中心仍然极具挑战性。鉴于连接到四配位硼原子的配体的不稳定性质，只有少数通过拆分或手性底物诱导的非对映选择性方法报道了对映富集的硼立体化合物。迄今为止，硼-立体化合物的催化不对称合成仍然未知。这里，我们通过不对称铜催化的叠氮化物-炔烃环加成（CuAAC）反应证明了硼-立体化合物的第一个催化对映选择性构建。这种对映选择性的 CuAAC 反应不仅可以高产率地获得各种新型高功能化的硼立体杂环，并且具有良好的对映选择性，而且还可以产生具有各种潜在应用前景的光学活性末端炔烃和三唑部分。手性四配位硼化合物的进一步转化产生了几个复杂的杂环实体，它们带有硼-立体中心，而不会损失对映体纯度。此外，还研究了所选四配位硼化合物的 X 射线结构、外消旋化障碍和

  DOI：

  10.1021/jacs.1c08482
• 作为产物：
  描述：

  4-氯丙酸 、 胆固醇 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 [(8R,9S,10S,13S,14R,15S,17R)-10,13-二甲基-17-[(2R)-6-甲基庚烷-2-基]-2,3,4,7,8,9,11,12,14,15,16,17-十二氢-1H-环戊并[a]菲-15-基]4-氯丁酸酯
  参考文献：
  名称：

  合成，新颖三和弦并在箱式位置胆固醇单元苝液晶的五元组的介晶和光物理性质†

  摘要：

  设计并合成了一系列在ylene位具有两个胆固醇单元或在with位和酰亚胺位都具有四个胆固醇单元的per衍生物的三单元组和五单元组，其产率为55-65％。研究了胆固醇取代基的不同数量和位置对介晶性质和光物理性质的影响。结果表明，与在酰亚胺位置具有烷基单元的类似per衍生物相比，在海湾位置具有烷基单元的per液晶不仅保持了优异的介晶性质，而且还大大增强了荧光。较高的胆固醇单位导致较低的中间相温度，较宽的相转移温度范围和较高的荧光。

  DOI：

  10.1039/c6ra27003d

文献信息

• Calix[4]resorcinarene-cholesterol columnar liquid crystals: Synthesis, mesomorphism and the influence of spacers on liquid crystalline behaviors
  作者：Chenyang Han、Hongyu Guo、Jianbin Lai、Fafu Yang

  DOI：10.1016/j.molliq.2017.01.111

  日期：2017.4

  Novel calix[4]resorcinarene derivatives with four cholesterol units bridging by soft spacers or rigid Schiff-base spacers were prepared in yields of 63–76%. The hexagonal columnar liquid crystalline behaviors were firstly observed for calix[4]resorcinarene derivatives. The mesomorphic properties were influenced greatly by the structures of spacers. The rigid spacers were favorable for enhancing the

  制备了具有四个胆固醇单元（由软间隔基或刚性席夫碱间隔基桥接）的新型杯[4]间苯二甲烯衍生物，产率为63–76％。首先观察到杯[4]间苯二酚衍生物的六方柱状液晶行为。介晶性能受垫片结构的影响很大。刚性间隔物有利于提高相变温度并扩大中间相的温度范围。
• Luminescent Helical Nanofiber Self-Assembled from a Cholesterol-Based Metalloamphiphile and Its Application in DNA Conformation Recognition
  作者：Hairui Lei、Jing Liu、Junlin Yan、Jingmiao Quan、Yu Fang

  DOI：10.1021/acs.langmuir.6b03181

  日期：2016.10.11

  helical nanofibers (d = 6 nm) in water. This synthetic multivalent nanoscale binding array displays powerful capability for the recognition of DNA conformations through a turn-on luminescence sensing mechanism. ssDNA-kit1 triggered a 26-fold increase in the luminescence intensity of TbL3+(I). Its corresponding G-quadruplex structure (G-quadruplex-kit1), however, induced a 6.6-fold enhancement under the same

  与纯有机两亲物相比，金属两亲物表现出独特的特征，包括发光，磁性和催化特性。但是，金属两亲分子的自组织通常是由疏溶剂作用驱动的。因此，烷基链和低聚乙二醇部分是驱动金属两亲物自组装的最常用聚集单元。如果合并其他非共价相互作用模式，我们预计将创建具有令人兴奋功能的新型金属-超分子结构。在这项工作中，设计并合成了一种新型的金属两亲物，它由一个Tb（III）配合物头部和一个胆固醇基单元（TbL 3+（I））组成。TbL 3+（I）自发地在水中自组装成螺旋纳米纤维（d = 6 nm）。这种合成的多价纳米级结合阵列显示出强大的能力，可通过开启式发光传感机制识别DNA构象。ssDNA-kit1触发了TbL 3+的发光强度增加了26倍（I）。但是，在相同条件下，其相应的G-四链体结构（G-quadruplex-kit1）诱导了6.6倍的增强。因此，TbL 3+（I）纳米纤维可以监测DNA折叠。相反，ssDN
• Ion complexation-controlled columnar mesophase of calix[4]arene–cholesterol derivatives with Schiff-base bridges
  作者：Xiaoyi Zhang、Hongyu Guo、Fafu Yang、Jin Yuan

  DOI：10.1016/j.tetlet.2016.01.047

  日期：2016.2

  Two novel calix[4]arene-cholesterol derivatives 7a and 7b with Schiff -base bridges were synthesized in yields of 70-80%. Their structural and conformational characterization had been achieved by NMR, MS, and elemental analysis. Their mesomorphic behaviors were studied by polarizing optical microscopy, differential scanning calorimetry, and X-ray diffraction. They possess mesomorphic properties with the molecular arrangement of the calixarene bowlic column and Schiff -based cholesterol unit as ancillary lateral column. The complexes of 7a and 7b with AgClO4 showed no mesophase. These results suggested that the mesophase of compounds 7a and 7b could be tuned by the ion-complexation behavior. (C) 2016 Elsevier Ltd. All rights reserved.
• Cholesteryl-containing ionic liquid crystals composed of alkylimidazolium cations and different anions
  作者：Xin Lan、Lu Bai、Xin Li、Shuang Ma、Xiaozhi He、Fanbao Meng

  DOI：10.1016/j.molstruc.2014.07.026

  日期：2014.10

  Cholesteryl-containing ionic liquid crystals (ILCs) 1-cholesteryloxycarbonylmethyl(propy1)-3methyl(butyl)imidazolium chlorides ([Ca-Me-Im]Cl, [Ca-Bu-Im]Cl, [Cb-Me-Irn]Cl and [Cb-Bu-Im1C1) and corresponding imidazolium tetrachloroaluminates ([Ca-Me-Im]AlC14, [Ca-Bu-Im]A1C14, [Cb-Me-Im]A1C14 and [Cb-Bu-Im]AlCl4) were synthesized in this work, and the chemical structure, LC behavior and ionic conductivity of all these ILCs were characterized by several technical methods. The imidazolium-based salts with Cl- ions showed chiral smectic A (S-A(*)) phase on both heating and cooling cycles, while the tetrachloroaluminates exhibited chiral nematic (N.) phase. The mesophase was confirmed by characteristic LC textures observed by polarizing optical microscopy and typical diffractogram obtained by X-ray diffraction measurements. The samples with similar cholesteryl-linkage component showed similar phase transition temperature and entropy, indicating the cholesteryl component influence predominately on the phase transition rather than alkyl substituents on the imidazole ring. The imidazolium tetrachloroaluminates display relatively low phase transition temperature compared with the precursor chlorides. The functional difference in LCl- behavior and ionic conductivity were discussed by investigated the structural difference between the cr-containing and AlCl4 containing materials. The imidazolium chlorides exhibited layer structure both in crystal and mesophase states, and should be organized with a 'headto-tail' organization to form interdigitated monolayer structures due to the tight ion pairs. But the imidazolium tetrachloroaluminates displayed layer structure only in crystal phase, and should be organized in 'head-to-head' arrangements form bilayer structures due to loose combination of ion pairs despite of hydrogen-bond and electrostatic attraction interaction. (C) 2014 Published by Elsevier B.V.
• Novel supramolecular liquid crystals: synthesis and mesomorphic properties of calix[4]arene-cholesterol derivatives
  作者：Hongyu Guo、Fafu Yang、Weiwei Liu、Jianbin Lai

  DOI：10.1016/j.tetlet.2014.12.137

  日期：2015.2

  The first calix[4]arene-cholesterol liquid crystals were designed and synthesized in yields of 50-80%. Structural and conformational characterization of these new compounds had been achieved by NMR, MS, and elemental analysis. Their liquid crystalline behaviors were studied by polarizing optical microscopy, differential scanning calorimetry, and X-ray diffraction. All calix[4]arene derivatives with two or four cholesterol units show excellent mesomorphic properties of the columnar molecular arrangement of the calixarenes bowlic columns with cholesterol units as ancillary lateral columns. The long spacer and more cholesterol units were favorable for excellent mesophase. (C) 2015 Published by Elsevier Ltd.