2-cyclohexylidene-3-trimethylsilyl-1-propanol | 306326-67-0

• 分子结构分类: 有机化合物 - 有机盐 - 有机金属盐
• 英文名称: 2-cyclohexylidene-3-trimethylsilyl-1-propanol
• 英文别名: 2-Cyclohexylidene-3-trimethylsilylpropan-1-ol
• CAS: 306326-67-0
• 化学式: C₁₂H₂₄OSi
• 分子量: 212.407
• InChiKey: BSAGCOSCIXHZKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.58
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-cyclohexylidene-3-trimethylsilyl-1-propanol 在 氯化二乙基铝 作用下， 以 吡啶 、 正己烷 、 二氯甲烷 为溶剂， 反应 0.25h， 生成 2-[(1-hydroxymethyl)cyclohexyl]-3-trimethylsilylprop-1-en-1-yl pivalate
  参考文献：
  名称：

  Synthesis of spirocyclic β-methylene-γ-lactone utilizing hydroxymethylation of functionalized allylsilane

  摘要：

  A new spiro-beta-methylene-gamma-lactone annulation reaction is addressed for the synthesis of 4-methylene-2-oxaspiro[4.5]decan-1-one and its derivatives. 2-Cyclohexylidene-3-trimethylsilylprop-1-yl pivalate, obtained from cyclohexanone, was hydroxymethylated followed by desilylation to afford 2-[(1-hydroxymethyl)cyclohexyl]prop-2-en-1-yl pivalate and its -1-en-1-yl isomer. The former was oxidized to carboxylic acid followed by lactonization to the above compound. It was found that the stereochemistry of the hydroxymethylation reaction depends on the substituent on the cyclohexane ring. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00403-9
• 作为产物：
  描述：

  3-trimethylsilyl-2-diethylphosphonopropionic acid ethyl ester 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 乙二醇二甲醚 、 乙醚 为溶剂， 反应 8.5h， 生成 2-cyclohexylidene-3-trimethylsilyl-1-propanol
  参考文献：
  名称：

  4-环亚烷基-5-（三甲基甲硅烷基）戊-1-烯-3-酮衍生物的纳扎罗夫环化。螺[4.5]癸烷，螺[4.4]壬烷及其衍生物的合成

  摘要：

  通过FeCl 3诱导的α-（三甲基甲硅烷基甲基）二乙烯基酮衍生物的纳扎罗夫环化反应合成了螺[4.5]癸烷和螺[4.4]壬烷环系统。发现产物的双键位置受α'-取代基的存在/不存在的控制，而三甲基甲硅烷基对于以高收率获得产物是必不可少的。具有外亚甲基的螺[4.4]壬烷进行了重排，形成双环[4.3.0]壬烷。

  DOI：

  10.1016/s0040-4020(00)00589-5

文献信息

• Synthesis of spiro[4.5]decane ring system through allylsilane promoted spiroannulation
  作者：Chiaki Kuroda、Yukari Hirono

  DOI：10.1016/0040-4039(94)85034-8

  日期：1994.9

  Spiro[4.5]decane ring system with methylene ketone on five membered ring was synthesized by Nazarov cyclization of α-(trimethylsilylmethyl)divinyl ketone derivatives.

  通过Nazarov环合α-（三甲基甲硅烷基甲基）二乙烯基酮衍生物的纳扎罗夫，合成了在五元环上带有亚甲基酮的螺[4.5]癸烷环系。
• Nazarov Cyclization of 4-Cycloalkylidene-5-(trimethylsilyl)pent-1-en-3-one Derivatives. Synthesis of Spiro[4.5]decane, Spiro[4.4]nonane, and Their Derivatives
  作者：Chiaki Kuroda、Hiroyuki Koshio、Akira Koito、Hiroshi Sumiya、Atsushi Murase、Yukari Hirono

  DOI：10.1016/s0040-4020(00)00589-5

  日期：2000.8

  Spiro[4.5]decane and spiro[4.4]nonane ring systems were synthesized by FeCl3-induced Nazarov cyclization of α-(trimethylsilylmethyl)divinyl ketone derivatives. It was found that the double bond position of the product is controlled by the presence/absence of α′-substituent, while trimethylsilyl group is essential to obtain the products in good yields. Spiro[4.4]nonanes having exo-methylene group underwent

  通过FeCl 3诱导的α-（三甲基甲硅烷基甲基）二乙烯基酮衍生物的纳扎罗夫环化反应合成了螺[4.5]癸烷和螺[4.4]壬烷环系统。发现产物的双键位置受α'-取代基的存在/不存在的控制，而三甲基甲硅烷基对于以高收率获得产物是必不可少的。具有外亚甲基的螺[4.4]壬烷进行了重排，形成双环[4.3.0]壬烷。
• Synthesis of spirocyclic β-methylene-γ-lactone utilizing hydroxymethylation of functionalized allylsilane
  作者：Chiaki Kuroda、Takahiro Kasahara、Kouki Akiyama、Takuma Amemiya、Takashi Kunishima、Yoshihiro Kimura

  DOI：10.1016/s0040-4020(02)00403-9

  日期：2002.5

  A new spiro-beta-methylene-gamma-lactone annulation reaction is addressed for the synthesis of 4-methylene-2-oxaspiro[4.5]decan-1-one and its derivatives. 2-Cyclohexylidene-3-trimethylsilylprop-1-yl pivalate, obtained from cyclohexanone, was hydroxymethylated followed by desilylation to afford 2-[(1-hydroxymethyl)cyclohexyl]prop-2-en-1-yl pivalate and its -1-en-1-yl isomer. The former was oxidized to carboxylic acid followed by lactonization to the above compound. It was found that the stereochemistry of the hydroxymethylation reaction depends on the substituent on the cyclohexane ring. (C) 2002 Elsevier Science Ltd. All rights reserved.