(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 acrylate | 26089-39-4

• 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
• 英文名称: (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 acrylate
• 英文别名: cholesteryl acrylate；(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 acrylate；Cholesterol acrylate；[(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] prop-2-enoate
• CAS: 26089-39-4
• 化学式: C₃₀H₄₈O₂
• 分子量: 440.71
• InChiKey: LBTKSYXEJYABAR-NXUCFJMCSA-N

物化性质

• 沸点：
  506.4±29.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  (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 acrylate 在 叔丁基过氧化氢 、 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以80%的产率得到(R)-Oxirane-2-carboxylic acid (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester
  参考文献：
  名称：

  一种强大的新型立体控制方法，用于亲电烯烃的环氧化

  摘要：

  无水四氢呋喃中的叔丁基氢过氧化物和烷基锂显示出以立体和区域特异性方式有效环氧化α，β-不饱和酯和砜，而手性醇的酯则经历了非对映选择性环氧化。

  DOI：

  10.1039/c39860001378
• 作为产物：
  描述：

  胆固醇 、 丙烯酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以61 %的产率得到(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 acrylate
  参考文献：
  名称：

  有机锗烷正交烯化

  摘要：

  芳基锗烷与烯烃在（准）卤素（C−I、C−Br、C−Cl、C−F、C−OTf、C−OSO 2 F）、硅烷和硼酸上的位点和电子选择性偶联衍生品已被报道。这种前所未有的基于[Ge]的氧化Heck偶联在室温下、在耐空气和无碱条件下高速进行。

  DOI：

  10.1002/anie.202310380

文献信息

• Mizoroki–Heck Reaction of Unstrained Aryl Ketones via Ligand-Promoted C–C Bond Olefination
  作者：Mei-Ling Wang、Hui Xu、Han-Yuan Li、Biao Ma、Zhen-Yu Wang、Xing Wang、Hui-Xiong Dai

  DOI：10.1021/acs.orglett.1c00296

  日期：2021.3.19

  Mizoroki–Heck reaction of unstrained aryl ketone with acrylate/styrene is accomplished via palladium-catalyzed ligand-promoted C–C bond cleavage. Various (hetero)aryl ketones are compatible in the reaction, affording the alkene product in good to excellent yields. Further applications in the late-stage olefination of some drugs, natural products, and fragrance-derived aryl ketones demonstrate the synthetic utility

  未应变的芳基酮与丙烯酸酯/苯乙烯的Mizoroki-Heck反应是通过钯催化的配体促进的C-C键裂解实现的。各种（杂）芳基酮在反应中是相容的，从而以良好至优异的产率提供了烯烃产物。在某些药物，天然产物和香料衍生的芳基酮的后期烯烃聚合中的进一步应用证明了该方案的合成效用。通过采用酮作为导向基团和离去基团二者，1,2- bifunctionalization经由顺序实现邻-C-H的烷基化/本位-Heck烯。
• Self-organization of cholesterol-side-chain liquid crystalline polymers by tailoring the main chain structure and flexible spacer length
  作者：Xiwen Yang、Shaonan Chen、Hang Luo、Haoran Xu、Sheng Chen

  DOI：10.1039/c8nj06168h

  日期：——

  the alkyl tail was overlapped (SmA2). Two-phase coexisting structures were observed in PCholAC-m (m = 8, 10), including a bilayer smectic A phase in which the alkyl tail was inserted into the mesogens (SmAd) and a single-layer smectic A phase in which the mesogens were overlapped (SmA1). Similar results were observed for PCholMC-m. Furthermore, PCholMC-0 possessed a stable bilayer SmA2 owing to the methyl

  三种侧链液晶聚合物（SCLCP），其中胆甾醇型液晶元（Chol）与聚丙烯酸酯（PCholAC- m），聚甲基丙烯酸酯（PCholMC- m）和聚（2-乙烯基苯-1,4-二酸酯）连接通过自由基聚合成功地合成了通过不同长度（m = 0、2、4、6、8和10）的亚甲基间隔基形成的（PCholVA- m）主链。使用DSC，POM和SAXS详细研究了聚合物的相行为和结构。结果表明，通过改变主链结构和间隔区长度，Chol-SCLCPs表现出有趣的自组织。所述聚合物最初形成近晶A相，除了没有液晶相的PCholAC-0以外。接下来，聚合物PCholAC-m（m＝ 2、4、6）形成两层近晶A相，其中烷基尾部重叠（SmA 2）。在PCholAC- m（m = 8，10）中观察到两相共存结构，包括双层近晶A相（其中烷基尾部插入到液晶元中）（SmA d）和单层近晶A相，其中液晶元重叠（SmA 1）。对于PCholMC-
• Glucosamine-6-phosphate synthase inhibiting C3-β-cholesterol tethered spiro heterocyclic conjugates: Synthesis and their insight of DFT and docking study
  作者：Govindasami Periyasami、Subban Kamalraj、Ramanathan Padmanaban、Santhakumar Yeswanth Kumar、Antony Stalin、Natarajan Arumugam、Raju Suresh Kumar、Mostafizur Rahaman、Periyan Durairaju、Abdulaziz Alrehaili、Ali Aldalbahi

  DOI：10.1016/j.bioorg.2019.102920

  日期：2019.7

  methodology. Stereochemistry of the spiranic cycloadducts has been established by spectroscopic analysis and the regioselectivity outcome of the spiro adducts has been accomplished by DFT calculations at B3LYP/6-31G (d,p) level study. In vitro antibacterial activity of the newly synthesized cycloadducts were evaluated against highly pathogenic Gram-positive and Gram-negative bacteria and the most active compounds

  通过C3-β-胆固醇铝酸酯与杂环二酮和三酮的反应，合成了一系列具有生物活性的羟吲哚，茚二酮和烯-1-酮的新的共价胆固醇-螺吡咯烷/吡咯烷核杂环杂化物。通过立体和区域选择性的1,3-偶极环加成方法以高收率获得了全部十六种化合物，为单一异构体。螺环加合物的立体化学已通过光谱分析确定，螺环加合物的区域选择性结果已通过在B3LYP / 6-31G（d，p）水平研究的DFT计算完成。评价了新合成的环加合物对高致病性革兰氏阳性和革兰氏阴性细菌以及活性最高的化合物5a，13的体外抗菌活性。
• Regioselective Synthesis and Structural Studies of Substituted γ-Hydroxybutenolides with Use of a Tandem Baylis−Hillman/Singlet Oxygenation Reaction
  作者：Santoshkumar N. Patil、Fei Liu

  DOI：10.1021/jo702762u

  日期：2008.6.1

  scope and limitations of a regioselective synthesis of either α- or β-substituted γ-hydroxybutenolides from 3-furfural and enones are described. The sequence features a Baylis−Hillman reaction followed by singlet oxygen oxidation with use of either an amine base or TBAF as the regioselectivity switches. Structural studies in solution on some of the resulting γ-hydroxybutenolides are also reported.

  描述了由3-糠醛和烯酮进行α-或β-取代的γ-羟基丁烯内酯的区域选择性合成的范围和局限性。该序列具有Baylis-Hillman反应，然后使用胺碱或TBAF作为区域选择性的开关，然后进行单线态氧氧化。还报道了在溶液中对某些所得的γ-羟基丁烯内酯的结构研究。
• Synthesis of Lipophilic 1-Substituted Diazen-1-ium-1,2-diolates.
  作者：Dominick C. ROSELLE、Daniel J. SMITH

  DOI：10.1248/cpb.45.747

  日期：——

  A new class of 1-substituted diazen-1-ium-1, 2-diolates (nitric oxide donors previously known as NONOates) were obtained by preparing esters of the naturally occurring polyamines putreanine (1) and spermic acid (2) with either cholesterol or hexadecanol. The syntheses of the following compounds and the corresponding NONOates are reported : cholesterylputreanine (5), dicholesterylspermate (6), hexadecanylputreanine (7), and dihexadecanylspermate (8).

  通过将天然存在的多胺——腐胺（1）和精胺酸（2）与胆固醇或十六醇形成酯，获得了一类新的1-取代二氮烯-1-鎓-1,2-二醇盐（以前称为NONOates的NO供体）。报道了以下化合物的合成及其相应的NONOates：胆固醇腐胺（5）、双胆固醇精胺酸盐（6）、十六烷基腐胺（7）和双十六烷基精胺酸盐（8）。