Silane, [(1-cyclohexyl-2-propenyl)oxy]trimethyl- | 138587-96-9

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: Silane, [(1-cyclohexyl-2-propenyl)oxy]trimethyl-
• 英文别名: 1-cyclohexylprop-2-enoxy(trimethyl)silane
• CAS: 138587-96-9
• 化学式: C₁₂H₂₄OSi
• 分子量: 212.407
• InChiKey: IMXLYJFDDZMCIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  Silane, [(1-cyclohexyl-2-propenyl)oxy]trimethyl- 在 PF6-2Pr3P 、 氢气 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 0.5h， 以96%的产率得到(Z)-1-cyclohexyl-1-(trimethylsilyloxy)-1-propene
  参考文献：
  名称：

  A stereoselective isomerization of allyl silyl ethers to (E)- or (Z)-silyl enol ethers using cationic iridium complexes

  摘要：

  一种阳离子铱配合物通过对[Ir(cod)2]PF6–2PPr3的氢化制备而成，发现其是初级烯丙基硅醚选择性异构化为(E)-烯醇醚和次级烯丙基醚异构化为(Z)-烯醇醚的优秀催化剂。

  DOI：

  10.1039/a802760i
• 作为产物：
  描述：

  环己烷基甲醛 在 咪唑 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.67h， 生成 Silane, [(1-cyclohexyl-2-propenyl)oxy]trimethyl-
  参考文献：
  名称：

  铁催化下 C-OH 裂解和硼转移相结合的烯丙醇立体选择性脱羟基硼酸制备 (E)-烯丙基硼酸酯

  摘要：

  铁催化的烯丙醇直接 S N 2' 脱羟基硼酸已被开发用于获得 ( E )-立体选择性烯丙基硼酸酯。具有多种结构和官能团的烯丙醇，特别是来自天然产物的烯丙醇，经历了平稳的转变。由烯丙醇和铁-硼中间体形成的六元环过渡态被证明是参与硼基团转移、C-OH键活化和立体选择性控制的关键成分。

  DOI：

  10.1021/acs.orglett.1c03359

文献信息

• [2-(Trimethylsilyl)ethylidene]tris(2-methylphenyl)phosphorane, a modified seyferth-wittig reagent for the stereoselective syntheses of -allyltrimethylsilanes
  作者：Hideo Iio、Masahiro Ishii、Masamitsu Tsukamoto、Takashi Tokoroyama

  DOI：10.1016/s0040-4039(00)82241-8

  日期：1988.1
• Nucleophilic additions to and reductiosn of 5-formyl-and 5-acyl-2-isoxazolines (4,5-dihydeoisoxazoles): a stereoselective route to β,γ-dihydroxy ketones
  作者：Dennis P. Curran、Jaincun Zhang

  DOI：10.1039/p19910002613

  日期：——

  Reductions of readily available 5-acyl-2-isoxazolines with L-Selectride follow the Felkin-Anh model and produce syn-5-hydroxyalkyl-2-isoxazolines with excellent (> 95:5) selectivities. Swern oxidation of 5-hydroxymethyl-2-isoxazolines, followed by direct addition of a Grignard reagent to the intermediate 5-formyl-2-isoxazolines, also follows the Felkin-Anh model and produces anti-5-hydroxyalkyl-2-isoxazolines with modest (80:20) to excellent (> 95:5) selectivity. In contrast, additions of Grignard reagents to 5-acyl-2-isoxazolines follow the chelation model, and give syn or anti products (depending on choice of acyl substituent and Grignard reagent) with good (90:10) to excellent selectivity. These selectivities are almost always far superior to those that can be obtained by direct nitrile oxide cycloaddition to a chiral allylic alcohol or ether. The resulting products are readily reduced to syn- or anti-beta,gamma-dihydroxy ketones. A speculative model to explain this surprising reversal in selectivity between formyl and acyl isoxazolines is proposed.
• IIO, HIDEO;ISHII, MASAHIRO;TSUKAMOTO, MASAMITSU;TOKOROYAMA, TAKASHI, TETRAHEDRON LETT., 29,(1988) N 46, C. 5965-5968
  作者：IIO, HIDEO、ISHII, MASAHIRO、TSUKAMOTO, MASAMITSU、TOKOROYAMA, TAKASHI

  DOI：——

  日期：——
• Stereoselective Dehydroxyboration of Allylic Alcohols to Access (<i>E</i>)-Allylboronates by a Combination of C–OH Cleavage and Boron Transfer under Iron Catalysis
  作者：Wei Su、Ting-Ting Wang、Xia Tian、Jian-Rong Han、Xiao-Li Zhen、Shi-Ming Fan、Ya-Xin You、Yu-Kun Zhang、Rui-Xiao Qiao、Qiushi Cheng、Shouxin Liu

  DOI：10.1021/acs.orglett.1c03359

  日期：2021.12.3

  Iron-catalyzed direct SN2′ dehydroxyboration of allylic alcohols has been developed to access (E)-stereoselective allylboronates. Allylic alcohols with diverse structures and functional groups, especially derived from natural products, underwent smooth transformation. The six-membered ring transition state formed by allylic alcohols and iron–boron intermediate was indicated to be the key component

  铁催化的烯丙醇直接 S N 2' 脱羟基硼酸已被开发用于获得 ( E )-立体选择性烯丙基硼酸酯。具有多种结构和官能团的烯丙醇，特别是来自天然产物的烯丙醇，经历了平稳的转变。由烯丙醇和铁-硼中间体形成的六元环过渡态被证明是参与硼基团转移、C-OH键活化和立体选择性控制的关键成分。
• A stereoselective isomerization of allyl silyl ethers to (E)- or (Z)-silyl enol ethers using cationic iridium complexes
  作者：Toshimichi Ohmura、Yasunori Yamamoto、Norio Miyaura

  DOI：10.1039/a802760i

  日期：——

  A cationic iridium complex, prepared via the hydrogenation of [Ir(cod)2]PF6–2PPr3 is found to be an excellent catalyst for the stereoselective isomerization of primary allyl silyl ethers to (E)-enol ethers and secondary allyl ethers to (Z)-enol ethers.

  一种阳离子铱配合物通过对[Ir(cod)2]PF6–2PPr3的氢化制备而成，发现其是初级烯丙基硅醚选择性异构化为(E)-烯醇醚和次级烯丙基醚异构化为(Z)-烯醇醚的优秀催化剂。