2-<(dimethylphenylsilyl)methyl>-2-propenyl-1-cyclopentanol | 127998-33-8

• 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: 2-<(dimethylphenylsilyl)methyl>-2-propenyl-1-cyclopentanol
• 英文别名: 1-[2-dimethyl(phenyl)silylmethylprop-2-en-1-yl]cyclopentan-1-ol；1-[2-[[Dimethyl(phenyl)silyl]methyl]prop-2-enyl]cyclopentan-1-ol
• CAS: 127998-33-8
• 化学式: C₁₇H₂₆OSi
• 分子量: 274.478
• InChiKey: VFZAPHVICYUPGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.85
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  苯基二甲基氯硅烷 生成 2-<(dimethylphenylsilyl)methyl>-2-propenyl-1-cyclopentanol
  参考文献：
  名称：

  Selective mono- and polymethylene homologations of copper reagents using (iodomethyl)zinc iodide

  摘要：

  A wide range of unsaturated aryl-, alkenyl-, alkynylcopper compounds can be selectively homologated by a methylene unit using (iodomethyl)zinc iodide or bis(iodomethyl)zinc. These reactions allow the generation of mixed allylic zinc-copper compounds which can be efficiently trapped with carbonyl compounds. An application to a general preparation of functionalized alpha-methylene-gamma-butyrolactones is described. The homologation of alkynylcoppers with (iodomethyl)zinc iodide allows a one-pot preparation of propargylic copper reagents which in the presence of a carbonyl compound provide various homopropargylic alcohols in excellent yields. In the absence of an electrophile, a clean quadruple methylene homologation of alkynylcoppers occurs to furnish dienic copper reagents. The homologation of other types of copper reagents is also possible, and carbanions at the alpha-position to amines as well as homoenolates of aldehydes or ketones can also be prepared by this method.

  DOI：

  10.1021/jo00062a010

文献信息

• Functionalised Allylsilanes from Silylcopper Reagents and Allene. A Useful Strategy for Cyclopentane Annulations
  作者：Asuncion Barbero、Carlos Garcı&#x;a、Francisco J. Pulido

  DOI：10.1016/s0040-4020(00)00129-0

  日期：2000.4

  allylsilane-containing divinyl ketones and oxoallylsilanes, respectively. They undergo highly stereocontrolled silicon-assisted intramolecular cyclizations when treated with protic or Lewis acid leading to cyclopentane ring-formation.

  使用苯基二甲基甲硅烷基铜或叔丁基二苯基甲硅烷基铜对丙二烯进行甲硅烷基化，然后与α，β-不饱和酰氯，醛或酮反应，分别得到含烯丙基硅烷的二乙烯基酮和氧代烯丙基硅烷。当用质子或路易斯酸处理时，它们会经历高度立体可控的硅辅助分子内环化反应，从而形成环戊烷环。
• Knochel, Paul; Achyutha Rao, Journal of the American Chemical Society, 1990, vol. 112, # 16, p. 6146 - 6148
  作者：Knochel, Paul、Achyutha Rao

  DOI：——

  日期：——
• KNOCHEL, PAUL;RAO, S. ACHYUTHA, J. AMER. CHEM. SOC., 112,(1990) N6, C. 6146-6148
  作者：KNOCHEL, PAUL、RAO, S. ACHYUTHA

  DOI：——

  日期：——
• Selective mono- and polymethylene homologations of copper reagents using (iodomethyl)zinc iodide
  作者：AchyuthaRao Sidduri、Michael J. Rozema、Paul Knochel

  DOI：10.1021/jo00062a010

  日期：1993.5

  A wide range of unsaturated aryl-, alkenyl-, alkynylcopper compounds can be selectively homologated by a methylene unit using (iodomethyl)zinc iodide or bis(iodomethyl)zinc. These reactions allow the generation of mixed allylic zinc-copper compounds which can be efficiently trapped with carbonyl compounds. An application to a general preparation of functionalized alpha-methylene-gamma-butyrolactones is described. The homologation of alkynylcoppers with (iodomethyl)zinc iodide allows a one-pot preparation of propargylic copper reagents which in the presence of a carbonyl compound provide various homopropargylic alcohols in excellent yields. In the absence of an electrophile, a clean quadruple methylene homologation of alkynylcoppers occurs to furnish dienic copper reagents. The homologation of other types of copper reagents is also possible, and carbanions at the alpha-position to amines as well as homoenolates of aldehydes or ketones can also be prepared by this method.