2-(Trimethylsilylmethyl)hept-1-en-4-ol | 189117-67-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(Trimethylsilylmethyl)hept-1-en-4-ol
• CAS: 189117-67-7
• 化学式: C₁₁H₂₄OSi
• 分子量: 200.396
• InChiKey: PXDRYXMXVYLHFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.43
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 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-(Trimethylsilylmethyl)hept-1-en-4-ol 在 三氟甲磺酸三甲基硅酯 、 zinc(II) chloride 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 (2R,6R)-4-methylidene-2-prop-2-enyl-6-propyloxane
  参考文献：
  名称：

  Synthesis of highly substituted 2,6-anti-configured tetrahydropyrans. First steps towards an efficient access to amphidinol 3 ring system

  摘要：

  Highly functionalised and polysubstituted tetrahydropyrans, akin to the middle core of the amphidinols, can be efficiently synthesised, with full stereocontrol and in good yields, using as key steps an anti-allylation reaction coupled with an intramolecular Sakurai cyclisation. Three approaches were devised in order to reach a broad range of substitution patterns. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.04.041
• 作为产物：
  描述：

  2-(氯甲基)烯丙基-三甲基硅烷 在 正丁基锂 、 sodium hydride 作用下， 反应 1.0h， 生成 2-(Trimethylsilylmethyl)hept-1-en-4-ol
  参考文献：
  名称：

  2-甲基硒代甲基烯丙基甲基硒化物的制备和合成应用。2-甲硅烷基甲基烯丙基锂的宝贵前体

  摘要：

  3-Lithio-2-[silylmethyl]propenes 很容易从 3-methylseleno-2-[silylmethyl]propenes 通过 C-Se 键的断裂制备，是制备各种功能化烯丙基硅烷的有用中间体。这些烯丙基硅烷是有趣的结构单元，例如用作通过分子内甲硅烷基改性 Sakurai (ISMS) 环化有效合成螺缩酮的退火剂。本文中描述的方法还提供了获得一系列杂取代甲基硒丙烯的便利途径，这些是一系列有用的杂取代烯丙基锂试剂的有价值的前体。最后，报道了从容易获得的 3-甲基硒基-2-[甲基硒基甲基]丙烯一步制备官能化烯丙基硅烷的方法。

  DOI：

  10.1055/s-1998-1915

文献信息

• [1,5]-Brook rearrangement: an overlooked but valuable silyl migration to synthesize configurationally defined vinylsilane. The unique steric and electronic effects of geminal bis(silane)
  作者：Lu Gao、Ji Lu、Zhenlei Song、Xinglong Lin、Yongjin Xu、Zhiping Yin

  DOI：10.1039/c3cc45002c

  日期：——

  geminal bis(silyl) homoallylic alcohol is described. The unique steric and electronic effects of geminal bis(silane) were found to be crucial for promoting this long-range silyl migration, as well as for facilitating the subsequent gamma/Z-selective addition of silyl allyllithium with carbonyl compounds to synthesize diverse configurationally defined Z-vinylsilanes.

  描述了双（甲硅烷基）双烯丙基醇双醇锂的不寻常的[1,5]-布鲁克重排。发现双（硅烷）双金属的独特空间和电子效应对于促进这种长距离的甲硅烷基迁移以及促进随后的甲硅烷基烯丙基锂与羰基化合物的γ/ Z选择性加成以合成各种构型定义至关重要Z-乙烯基硅烷。
• Synthesis of Functionalized Allylsilanes Using 3-(Stannyl)-2-(silylmethyl)propene
  作者：Kyung-Tae Kang、Tae Myung Sung、Jun Keun Kim、Yong Mok Kwon

  DOI：10.1080/00397919708003354

  日期：1997.4

  Reactions of 3-tributylstannyl-2-(trimethylsilylmethyl)propene with acid chlorides or aldehydes proceed smoothly without any catalytic activation to afford allylsilanes bearing various functionalities.
• Synthesis of highly substituted 2,6-anti-configured tetrahydropyrans. First steps towards an efficient access to amphidinol 3 ring system
  作者：Christophe Dubost、Istvan E. Markó、Justin Bryans

  DOI：10.1016/j.tetlet.2005.04.041

  日期：2005.6

  Highly functionalised and polysubstituted tetrahydropyrans, akin to the middle core of the amphidinols, can be efficiently synthesised, with full stereocontrol and in good yields, using as key steps an anti-allylation reaction coupled with an intramolecular Sakurai cyclisation. Three approaches were devised in order to reach a broad range of substitution patterns. (c) 2005 Elsevier Ltd. All rights reserved.
• Preparation and Synthetic Utility of 2-Methylselenomethyl Allyl Methyl Selenide. A Valuable Precursor to 2-Silylmethylallyllithiums
  作者：Alain Krief

  DOI：10.1055/s-1998-1915

  日期：1998.11

  3-Lithio-2-[silylmethyl]propenes, easily prepared from 3-methylseleno-2-[silylmethyl]propenes by the cleavage of the C-Se bond, are useful intermediates for the preparation of a variety of functionalised allylsilanes. These allylsilanes are interesting building blocks, used for example, as annelating agents in the efficient synthesis of spiroketals by the Intramolecular Silyl-Modified Sakurai (ISMS)

  3-Lithio-2-[silylmethyl]propenes 很容易从 3-methylseleno-2-[silylmethyl]propenes 通过 C-Se 键的断裂制备，是制备各种功能化烯丙基硅烷的有用中间体。这些烯丙基硅烷是有趣的结构单元，例如用作通过分子内甲硅烷基改性 Sakurai (ISMS) 环化有效合成螺缩酮的退火剂。本文中描述的方法还提供了获得一系列杂取代甲基硒丙烯的便利途径，这些是一系列有用的杂取代烯丙基锂试剂的有价值的前体。最后，报道了从容易获得的 3-甲基硒基-2-[甲基硒基甲基]丙烯一步制备官能化烯丙基硅烷的方法。