2,2-dichloro-1-methylcyclopropyl(pentadeuteriophenyl)methanone | 850785-67-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-dichloro-1-methylcyclopropyl(pentadeuteriophenyl)methanone
• 英文别名: (2,2-Dichloro-1-methylcyclopropyl)-(2,3,4,5,6-pentadeuteriophenyl)methanone
• CAS: 850785-67-0
• 化学式: C₁₁H₁₀Cl₂O
• 分子量: 234.066
• InChiKey: MQUVHBBGJWTQJI-VIQYUKPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,2-dichloro-1-methylcyclopropyl(pentadeuteriophenyl)methanone 在 叔丁基二甲硅基三氟甲磺酸酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 4,4-dichloro-1-(4-chlorophenyl)-2-methyl-1-(pentadeuteriophenyl)-1,3-butadiene
  参考文献：
  名称：

  Regiocontrolled benzannulation of diaryl(gem-dichlorocyclopropyl)methanols for the synthesis of “unsymmetrically” substituted α-arylnaphthalenes

  摘要：

  Aryl(1)(aryl(2))(gem-dichlorocyclopropyl)methanols 1 underwent alternative benzannulation to give ''unsymmetrically'' substituted 1-(aryl(1))-4-chloronaphthalenes 2/A catalyzed by SnCl4 or TiCl4 and to give 1-(aryl(2))-4-chloronaphthalenes 2/B catalyzed by silyl triflates with good to excellent selectivities. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01713-9
• 作为产物：
  描述：

  2,2-二氯-1-甲基-环丙烷羰酰氯 、 pentadeuteriophenyllithium 生成 2,2-dichloro-1-methylcyclopropyl(pentadeuteriophenyl)methanone
  参考文献：
  名称：

  Regiocontrolled benzannulation of diaryl(gem-dichlorocyclopropyl)methanols for the synthesis of “unsymmetrically” substituted α-arylnaphthalenes

  摘要：

  Aryl(1)(aryl(2))(gem-dichlorocyclopropyl)methanols 1 underwent alternative benzannulation to give ''unsymmetrically'' substituted 1-(aryl(1))-4-chloronaphthalenes 2/A catalyzed by SnCl4 or TiCl4 and to give 1-(aryl(2))-4-chloronaphthalenes 2/B catalyzed by silyl triflates with good to excellent selectivities. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01713-9

文献信息

• Regiocontrolled Benzannulation of Diaryl(<i>gem</i>-dichlorocyclopropyl)methanols for the Synthesis of Unsymmetrically Substituted α-Arylnaphthalenes:  Application to Total Synthesis of Natural Lignan Lactones
  作者：Yoshinori Nishii、Taichi Yoshida、Hirofumi Asano、Kazunori Wakasugi、Jun-ichi Morita、Yoshifumi Aso、Eri Yoshida、Jiro Motoyoshiya、Hiromu Aoyama、Yoo Tanabe

  DOI：10.1021/jo047751u

  日期：2005.4.1

  synthesis of highly substituted α-arylnaphthalene analogues has been developed utilizing Lewis acid-promoted regiocontrolled benzannulation of aryl(aryl‘)-2,2-dichlorocyclopropylmethanols (aryl ≠ aryl‘; abbreviated as AACMs). Both AACM diastereomers were easily prepared via highly stereoselective addition (>95/5) of ArLi to gem-dichlorocyclopropropyl aryl‘ ketones. The choice of Lewis acids determined

  利用路易斯酸促进的芳基（芳基）-2，2-二氯环丙基甲醇（芳基≠芳基；缩写为AACMs）的路易斯酸区域控制的苯环已开发出高取代的α-芳基萘类似物的有效合成方法。两种AACM非对映异构体都可以通过将ArLi高​​度立体选择性地加成（> 95/5）到宝石-dichlorocyclopropropyl aryl'ketones上来制备。路易斯酸的选择决定了本苯并环的环化区域选择性。TiCl 4和SnCl 4使用螯合途径，而甲硅烷基三氟甲磺酸盐使用非螯合途径以40-91％的产率提供不对称取代的区域异构α-芳基萘，具有中等至出色的区域选择性（TiCl 4或SnCl 4 ; > 99 / 1-3 / 1，TBDMSOTf；> 1 / 99-1 / 4）。因此，通过选择反应顺序的顺序或合适的催化剂，可将α-芳基或α-芳基'部分（辅助芳基）引入α-芳基萘。证明了本方法在不对称取代的天然木脂素内酯，justicidin
• Regiocontrolled benzannulation of diaryl(gem-dichlorocyclopropyl)methanols for the synthesis of “unsymmetrically” substituted α-arylnaphthalenes
  作者：Yoshinori Nishii、Taichi Yoshida、Yoo Tanabe

  DOI：10.1016/s0040-4039(97)01713-9

  日期：1997.10

  Aryl(1)(aryl(2))(gem-dichlorocyclopropyl)methanols 1 underwent alternative benzannulation to give ''unsymmetrically'' substituted 1-(aryl(1))-4-chloronaphthalenes 2/A catalyzed by SnCl4 or TiCl4 and to give 1-(aryl(2))-4-chloronaphthalenes 2/B catalyzed by silyl triflates with good to excellent selectivities. (C) 1997 Elsevier Science Ltd.