Benzoic acid 1-methyl-cyclopropylmethyl ester | 121416-58-8

• 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: Benzoic acid 1-methyl-cyclopropylmethyl ester
• 英文别名: (1-Methylcyclopropyl)methyl benzoate
• CAS: 121416-58-8
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: QSONQVYSNQTCCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-bromo-2-methyl-1,2-epoxybutane 、 苯甲酰氯 在 铜 、 三苯基膦 作用下， 生成 Benzoic acid 1-methyl-cyclopropylmethyl ester
  参考文献：
  名称：

  由活化的铜和环氧烷基溴化物直接形成环氧烷基铜试剂及其分子内环化

  摘要：

  环氧烷基铜化合物很容易通过将活性铜直接氧化加成到环氧烷基卤化物中来制备。描述了经由环氧化物裂解过程的环氧烷基铜试剂的分子内环化。重要的是，溴环氧化物中可以存在许多官能团，从而产生高度官能化的碳环。该环化的区域选择性受连接链长度，取代模式，反应溶剂和用于生成铜的CuI-膦配合物的影响。

  DOI：

  10.1016/s0040-4039(00)82446-6

文献信息

• Direct formation of epoxyalkylcopper reagents from activated copper and epoxyalkyl bromides and their intranolecular cyclizations
  作者：Tse-Chong Wu、Reuben D Rieke

  DOI：10.1016/s0040-4039(00)82446-6

  日期：——

  Epoxyalkylcopper compounds have readily been prepared by the direct oxidative addition of active copper to epoxyalkyl halides. The intramolecular cyclization of the epoxyalkylcopper reagents via an epoxide cleavage process is described. Significantly, many functional groups can be present in the bromoepoxides yielding highly functionalized carbocycles. The regioselectivity of this cyclization is affected

  环氧烷基铜化合物很容易通过将活性铜直接氧化加成到环氧烷基卤化物中来制备。描述了经由环氧化物裂解过程的环氧烷基铜试剂的分子内环化。重要的是，溴环氧化物中可以存在许多官能团，从而产生高度官能化的碳环。该环化的区域选择性受连接链长度，取代模式，反应溶剂和用于生成铜的CuI-膦配合物的影响。
• Rieke, Reuben D.; Wu, Tse-Chong; Stinn, Dean E., Synthetic Communications, 1989, vol. 19, # 11-12, p. 1833 - 1840
  作者：Rieke, Reuben D.、Wu, Tse-Chong、Stinn, Dean E.、Wehmeyer, Richard M.

  DOI：——

  日期：——
• Direct formation and reaction of thienyl-based organocopper reagents
  作者：Reuben D. Rieke、Walter R. Klein、Tse Chong Wu

  DOI：10.1021/jo00061a024

  日期：1993.4

  The preparation of a highly reactive zerovalent copper complex by the direct reduction of lithium (2-thienylcyano)cuprate with preformed lithium naphthalenide is described. This active copper species oxidatively adds to carbon-halogen bonds to form organocopper reagents. The ability to directly form the organocopper reagent from organic halides and active copper allows for the incorporation of a wide variety of functionalities to be present in the organic halides and the organocopper reagents. Significantly, this formulation of active copper was able to oxidatively add to allyl chlorides and acetates at low temperatures to allow the direct formation of allylic organocopper reagents without Wurtz-type homocoupling. These functionalized organocopper compounds are able to undergo a variety of reactions, such as cross-coupling with acid chlorides, 1,4-conjugate addition with alpha,beta-unsaturated carbonyl compounds, and intermolecular and intramolecular epoxide-opening reactions. Subsequently, this copper species avoids the use of phosphine ligands affording the product isolation much more convenient than with phosphine-based organocopper reagents.