1-(4-methoxyphenyl)-2,3,3-trichloro-1-hydroxy-2-propene | 114703-29-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(4-methoxyphenyl)-2,3,3-trichloro-1-hydroxy-2-propene
• 英文别名: p-Methoxyphenyltrichlorovinyl carbinol；2,3,3-trichloro-1-(4-methoxyphenyl)prop-2-en-1-ol
• CAS: 114703-29-6
• 化学式: C₁₀H₉Cl₃O₂
• 分子量: 267.539
• InChiKey: YEZYMLZJSTZDJZ-UHFFFAOYSA-N

物化性质

• 沸点：
  375.8±42.0 °C(predicted)
• 密度：
  1.420±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  甲醇 、 1-(4-methoxyphenyl)-2,3,3-trichloro-1-hydroxy-2-propene 在 硫酸 、 水 作用下， 生成 (Z)-2-chloro-3-(4-methoxyphenyl)acrylic acid methyl ester
  参考文献：
  名称：

  Synthesis of .alpha.-halocinnamate esters via solvolytic rearrangement of trichloroallyl alcohols

  摘要：

  Aryl trichlorovinyl ketones undergo regioselective reduction to the corresponding carbinols with sodium borohydride in alcoholic solvents and are transformed to the (Z)-alpha-chlorocinnamate ester derivatives via an acid-catalyzed allylic rearrangement. Michael addition of ammonia to these ester derivatives affords cis- and/or trans-aziridine amides. The facile rearrangement allows the synthesis of d,l-phenylalanine derived from perchloroethylene and toluene.

  DOI：

  10.1021/jo00010a027
• 作为产物：
  描述：

  1-(4-methoxyphenyl)-2,3,3-trichloro-1-oxopropene 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以99%的产率得到1-(4-methoxyphenyl)-2,3,3-trichloro-1-hydroxy-2-propene
  参考文献：
  名称：

  Synthesis of .alpha.-halocinnamate esters via solvolytic rearrangement of trichloroallyl alcohols

  摘要：

  Aryl trichlorovinyl ketones undergo regioselective reduction to the corresponding carbinols with sodium borohydride in alcoholic solvents and are transformed to the (Z)-alpha-chlorocinnamate ester derivatives via an acid-catalyzed allylic rearrangement. Michael addition of ammonia to these ester derivatives affords cis- and/or trans-aziridine amides. The facile rearrangement allows the synthesis of d,l-phenylalanine derived from perchloroethylene and toluene.

  DOI：

  10.1021/jo00010a027

文献信息

• Process for the preparation of .alpha.-halocinnamate esters
  申请人：The Dow Chemical Company

  公开号：US04727181A1

  公开（公告）日：1988-02-23

  Prepare esters of .alpha.-halocinnamic acid and related compounds in high yield under relatively mild conditions.

  在相对温和的条件下高产地制备.alpha.-卤代肉桂酸及相关化合物的酯。
• US4727181A
  申请人：——

  公开号：US4727181A

  公开（公告）日：1988-02-23
• Synthesis of .alpha.-halocinnamate esters via solvolytic rearrangement of trichloroallyl alcohols
  作者：William J. Kruper、Albert H. Emmons

  DOI：10.1021/jo00010a027

  日期：1991.5

  Aryl trichlorovinyl ketones undergo regioselective reduction to the corresponding carbinols with sodium borohydride in alcoholic solvents and are transformed to the (Z)-alpha-chlorocinnamate ester derivatives via an acid-catalyzed allylic rearrangement. Michael addition of ammonia to these ester derivatives affords cis- and/or trans-aziridine amides. The facile rearrangement allows the synthesis of d,l-phenylalanine derived from perchloroethylene and toluene.