2-(4’-t-butyldimethylsilyloxyphenyl)-1-iodoethane | 185063-17-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(4’-t-butyldimethylsilyloxyphenyl)-1-iodoethane
• 英文别名: tert-butyl[4-(2-iodoethyl)phenoxy]dimethylsilane；4-tert-butyl-dimethyl-silyloxy-phenethyl iodide；4-t-butyldimethylsilyloxyphenethyl iodide；Tert-butyl-[4-(2-iodoethyl)phenoxy]-dimethylsilane
• CAS: 185063-17-6
• 化学式: C₁₄H₂₃IOSi
• 分子量: 362.326
• InChiKey: MYXVPPYKRGXFRP-UHFFFAOYSA-N

物化性质

• 沸点：
  326.7±35.0 °C(Predicted)
• 密度：
  1.278±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.05
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(4’-t-butyldimethylsilyloxyphenyl)-1-iodoethane 在 盐酸 、 sodium hydroxide 、 正丁基锂 、 二异丙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 水 为溶剂， 反应 10.0h， 生成 L-homotyrosine methyl ester
  参考文献：
  名称：

  Kearney, Patrick C.; Nowak, Mark W.; Zhong, Wenge, Molecular Pharmacology, 1996, vol. 50, # 5, p. 1401 - 1412

  摘要：

  DOI：
• 作为产物：
  描述：

  methanesulfonic acid 2-[4-(tert-butyl-dimethyl-silyloxy)-phenyl]-ethyl ester 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 14.0h， 以78%的产率得到2-(4’-t-butyldimethylsilyloxyphenyl)-1-iodoethane
  参考文献：
  名称：

  用作神经酰胺合酶1抑制剂的AAL（S）类似物的合成和生物学评估†

  摘要：

  描述了一种收敛的合成方法，以接近疏水性尾部类似物和AAL（S）的头部基团修饰。评价了合成的类似物抑制神经酰胺合酶1的能力以及在K562细胞中的细胞毒性。我们的结果确定了无细胞毒性但仍能抑制CerS1的抑制剂。

  DOI：

  10.1039/c5ob01931a

文献信息

• Synthesis and Application of Phosphorus Dendrimer Immobilized Azabis(oxazolines)
  作者：Anja Gissibl、Clément Padié、Markus Hager、Florian Jaroschik、Ramesh Rasappan、Erick Cuevas-Yañez、Cédric-Olivier Turrin、Anne-Marie Caminade、Jean-Pierre Majoral、Oliver Reiser

  DOI：10.1021/ol071128p

  日期：2007.7.1

  Phosphorus dendrimer immobilized azabis(oxazoline) ligands can be efficiently synthesized up to the third generation with 48 ligand molecules being attached to the periphery using click chemistry. The so-assembled macromolecules were evaluated in copper(II)-catalyzed asymmetric benzoylations, showing good yields and enantioselectivities. Moreover, the copper(II)-catalysts could be readily recovered

  磷树枝状聚合物固定的氮杂双（恶唑啉）配体可通过点击化学有效合成至第三代，其中48个配体分子附着在外围。如此组装的大分子在铜（II）催化的不对称苯甲酰化反应中进行了评估，显示出良好的收率和对映选择性。而且，铜（II）-催化剂可以容易地回收并在数个循环中重复使用。与相同类型的MeOPEG或聚苯乙烯结合的配体相反，树状配体的球形结构似乎阻止了三唑部分在催化中的干扰。
• B(C₆F₅)₃‐Catalyzed [2+3]‐Cyclative <i>o</i>,<i>m</i>‐diC‐H Functionalization of Phenols
  作者：Jingyan Luo、Zhou Luo、Biqi Zhang、Qiuyu Zhao、Lu Liu、Yuanyuan Liu

  DOI：10.1002/chem.202301595

  日期：2023.12.19

  B(C6F5)3-catalyzed highly chemoselective [2+3]-cyclative diC−H functionalization of phenols tethered with propargylic ether motifs was developed for the synthesis of polycyclic compounds. Derivatizations of the phenol-OH group demonstrated the good variability of the cyclization products, indicating the potential application of this methodology in the preparation of other types of polycyclic compounds.

  AB(C 6 F 5 ) 3催化的与炔丙基醚基序相连的酚的高度化学选择性的[2+3]-环化二C−H官能化被开发用于多环化合物的合成。酚-OH基团的衍生化证明了环化产物具有良好的可变性，表明该方法在制备其他类型的多环化合物中具有潜在的应用前景。
• TX-2152: A conformationally rigid and electron-rich diyne analogue of FTY720 with in vivo antiangiogenic activity
  作者：Shinichi Nakayama、Yoshihiro Uto、Kanako Tanimoto、Yasuhiro Okuno、Yuki Sasaki、Hideko Nagasawa、Eiji Nakata、Ken Arai、Kaori Momose、Tetsuro Fujita、Toshihiro Hashimoto、Yasuko Okamoto、Yoshinori Asakawa、Satoru Goto、Hitoshi Hori

  DOI：10.1016/j.bmc.2008.07.003

  日期：2008.8

  We designed FTY720 analogues with conformationally rigid and electron-rich acetylenic chains as anti-angiogenic agents ( the monoyne 1: TX-2148, the diyne 2: TX-2152, the triyne 3: TX-2256). Molecular orbital ( MO) calculations of our designed acetylenic analogues and FTY720 showed that the localization of the lowest unoccupied MO and the highest occupied MO increased from phenyl ring to acetylenic chain compared with that of FTY720. These acetylenic analogues were synthesized from p-hydroxyphenylethanol as a starting material. The construction of the acetylenic chain was carried out by an iterative strategy using a Sonogashira cross-coupling reaction and desilylative bromination in two steps. The corresponding overall yields of the monoyne 1, the diyne 2, and the triyne 3 were 27% ( 11 steps), 13% ( 13 steps), and 10% ( 15 steps). The in vivo antiangiogenic activities of these acetylenic analogues and FTY720 were evaluated by the chick embryo chorioallantoic membrane ( CAM) assay and compared to the activities of the known antiangiogenic agent TNP-470. The diyne 2 showed more potent antiangiogenic activity ( 90% inhibition) than FTY720 ( 77% inhibition) and other acetylenic analogues ( the monoyne 1: 42% inhibition, the triyne 3: 60% inhibition), and TNP-470 ( 82% inhibition) at a dose of 10 mu g/CAM, without showing toxicity. The diyne 2 also had potent inhibitory activity at a dose of 5 and 2.5 mu g/CAM. These results indicate that the flexibility of C8 alkyl chain of FTY720 is not required for its antiangiogenic activity. We suggest that the diyne 2 ( TX-2152) may be a promising candidate as an antiangiogenic agent for antineoplastic drug discovery. (C) 2008 Elsevier Ltd. All rights reserved.
• Stereoselective synthesis of bioactive natural spiroacetals aculeatins A and B
  作者：Biswanath Das、Martha Krishnaiah、Chithaluri Sudhakar

  DOI：10.1016/j.bmcl.2010.01.162

  日期：2010.4

  The stereoselective synthesis of two naturally occurring bioactive spiroacetals, aculeatins A and B has been accomplished using 1-tetradecanal as the starting material. The sequence introduces diastereoselective iodine-induced electrophilic cyclization and ring opening of epoxide with 1,3-dithiane as the key steps. (C) 2010 Elsevier Ltd. All rights reserved.