2-chloro-6-(1-hydroxyallyl)phenol | 911817-91-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-chloro-6-(1-hydroxyallyl)phenol
• 英文别名: 2-chloro-6-(1-hydroxy-2-propenyl)phenol；2-chloro-6-(1-hydroxyprop-2-enyl)phenol
• CAS: 911817-91-9
• 化学式: C₉H₉ClO₂
• 分子量: 184.622
• InChiKey: HOGMXFIXGFAILC-UHFFFAOYSA-N

物化性质

• 沸点：
  272.6±10.0 °C(Predicted)
• 密度：
  1.295±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-chloro-6-(1-hydroxyallyl)phenol 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Palladium‐Catalyzed Enantioselective [4+2] Cycloaddition of 4‐Vinylbenzodioxinones with Barbiturate‐Derived Alkenes: Con‐struction of Chiral Spirobarbiturate−Chromanes

  摘要：

  In this paper, Pd‐catalyzed [4+2] decarboxylative cycloaddition of 4‐vinylbenzodioxinones with barbiturate‐derived alkenes has been developed, leading to various spirobarbiturate−chromane derivatives in high yields with excellent diastereo‐ and enantioselectivities. The scale‐up reaction and further derivation of the product were demonstrated. A plausible reaction mechanism was also proposed.

  DOI：

  10.1002/chem.202400302
• 作为产物：
  描述：

  3 -氯- 2 -羟基苯 、 乙烯基氯化镁 以 四氢呋喃 为溶剂， 反应 0.5h， 以96%的产率得到2-chloro-6-(1-hydroxyallyl)phenol
  参考文献：
  名称：

  铁（III）络合物催化的烯丙基环化反应生成的2H-Chromenes

  摘要：

  据报道，一种基于铁（III）络合物催化的2-（1-羟基烯丙基）苯酚环化的简单方法可以使用多种2 H-色烯。该方法应用于天然产物替弗洛韦汀B的全合成。

  DOI：

  10.1002/adsc.201500058

文献信息

• Production Process of cyclopropylphenol derivatives
  申请人：Tsukamoto Yoshihisa

  公开号：US20090054681A1

  公开（公告）日：2009-02-26

  A process for producing a cyclopropylphenol represented by of formula (10): wherein R 1 , R 2 , R 3 and R 4 each may represent a hydrogen; Z represents a hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or phenyl; and Y 1 , Y 2 and Y 3 each may represent a hydrogen; by reacting a compound of formula (7): wherein X represents a halogen; and V represents a hydrogen or —W—R 5 , with a metal, metal salt or organometallic compound of formula (8): M 2 to obtain a compound of formula (9): and obtaining a compound represented by general of formula (10) by hydrolysis in the case wherein V represents —W—R 5 , wherein W is CO, SO or SO 2 and R 5 is alkyl, haloalkyl, cycloalkyl, alkenyl, alkynyl, phenyl, alkoxy or haloalkoxy.

  一种生产环丙基酚的方法，其化学式表示为(10): 其中，R1、R2、R3和R4均可代表氢原子；Z代表氢原子、烷基、烯基、炔基、环烷基或苯基；Y1、Y2和Y3均可代表氢原子。该方法通过将化合物(7)： 其中，X代表卤素；V代表氢原子或-W-R5，与化合物(8)： M2代表金属、金属盐或有机金属化合物，反应得到化合物(9)： 在V代表-W-R5的情况下，通过水解得到化学式为(10)的化合物，其中W为CO、SO或SO2，R5为烷基、卤代烷基、环烷基、烯基、炔基、苯基、烷氧基或卤代烷氧基。
• Process for producing cyclopropylphenol derivative
  申请人：Mitsui Chemicals Agro, Inc.

  公开号：US07629494B2

  公开（公告）日：2009-12-08

  A process for producing a cyclopropylphenol represented by of formula (10): wherein R1, R2, R3 and R4 each may represent a hydrogen; Z represents a hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or phenyl; and Y1, Y2 and Y3 each may represent a hydrogen; by reacting a compound of formula (7): wherein X represents a halogen; and V represents a hydrogen or —W—R5, with a metal, metal salt or organometallic compound of formula (8): M2 to obtain a compound of formula (9): and obtaining a compound of formula (10) by hydrolysis in the case wherein V represents —W—R5, wherein W is CO, SO or SO2 and R5 is alkyl, haloalkyl, cycloalkyl, alkenyl, alkynyl, phenyl, alkoxy or haloalkoxy.

  一种制备环丙基苯酚的方法，其化学式表示为（10）：其中R1、R2、R3和R4均可表示氢；Z表示氢、烷基、烯基、炔基、环烷基或苯基；Y1、Y2和Y3均可表示氢；通过将化合物（7）：其中X表示卤素；V表示氢或-W-R5，与化合物（8）的金属、金属盐或有机金属化合物反应，得到化合物（9）：并在V表示-W-R5的情况下通过水解得到化合物（10），其中W为CO、SO或SO2，R5为烷基、卤代烷基、环烷基、烯基、炔基、苯基、烷氧基或卤代烷氧基。
• 4-Vinylbenzodioxinones as a new type of precursor for palladium-catalyzed (4+3) cycloaddition of azomethine imines
  作者：Yi Tang、Rulei Zhang、Yujie Dong、Songcheng Yu、Yongjun Wu、Yumei Xiao、Hongchao Guo

  DOI：10.1039/d3cc06012h

  日期：——

  In this paper, benzo-fused cyclic carbonates were designed and synthesized as a new type of precursor of π-allylpalladium zwitterionic intermediates, and were applied in Pd-catalyzed diastereo- and enantioselective (4+3) cycloaddition with C,N-cyclic azomethine imines, leading to various biologically important 1,3,4-benzoxadiazepine derivatives in 43–99% yields with 6 : 1 to >20 : 1 dr and up to 95%

  本文设计并合成了苯并稠合环状碳酸酯作为π-烯丙基钯两性离子中间体的新型前体，并将其应用于Pd催化的C , N-环状偶氮甲碱的非对映和对映选择性(4+3)环加成反应。亚胺，产生各种具有生物学重要意义的 1,3,4-苯并恶二氮杂卓衍生物，产率 43-99%，dr 为 6:1 至 >20:1，ee 高达 95%。
• PROCESS FOR PRODUCING CYCLOPROPYLPHENOL DERIVATIVE
  申请人：Sankyo Agro Company, Limited

  公开号：EP1880987A1

  公开（公告）日：2008-01-23

  An object of the present invention is to find a method for easily synthesizing cyclopropylphenol derivatives. The object of the present invention is to find a process for producing a cyclopropylphenol derivative represented by general formula (10): [wherein R1, R2, R3 and R4 each independently represent a hydrogen atom or the like; Z represents a hydrogen atom or the like; and Y1, Y2 and Y3 each independently represent a hydrogen atom or the like]; and solved by the process comprising reacting a compound represented by general formula (7): [wherein each of the symbols are the same as previously defined; X represents a halogen atom; and V represents a hydrogen atom or the like], with a metal, metal salt or organometallic compound represented by general formula (8): M2 to obtain a compound represented by general formula (9): [wherein each of the symbols are the same as previously defined] and obtaining a compound represented by general formula (10) by hydrolysis in the case V represents the group, -W-R5.

  本发明的目的是找到一种易于合成环丙基苯酚衍生物的方法。本发明的目的是找到一种生产通式（10）所代表的环丙基苯酚衍生物的工艺： [其中 R1、R2、R3 和 R4 各自独立地代表氢原子或类似物；Z 代表氢原子或类似物；Y1、Y2 和 Y3 各自独立地代表氢原子或类似物]； 并通过使通式 (7) 所代表的化合物发生反应的过程来解决： [其中各符号与前面定义的相同；X 代表卤素原子；V 代表氢原子或类似物]、 用通式（8）代表的金属、金属盐或有机金属化合物：M2，得到通式（9）所代表的化合物： [在 V 代表基团-W-R5 的情况下，通过水解得到通式（10）代表的化合物。
• Palladium-Catalyzed (4 + 1) Annulation of 4-Vinylbenzodioxinones with Sulfur Ylides: Diastereoselective Synthesis of Dihydrobenzofuran Derivatives
  作者：Yi Tang、Xiaojing Sun、Yu Tan、Lan Wang、Yanmei Xiong、Hongchao Guo

  DOI：10.1021/acs.joc.4c00912

  日期：2024.6.21

  Palladium-catalyzed (4 + 1) annulation of 4-vinylbenzodioxinones with sulfur ylides has been developed to afford various dihydrobenzofuran derivatives in moderate to high yields with excellent diastereoselectivities. The scale-up reaction and further derivations of the product worked well, demonstrating the application potential of the current reaction in organic synthesis.

  钯催化的 4-乙烯基苯并二恶酮与硫叶立德的 (4 + 1) 成环反应已被开发出来，可以以中等至高产率提供各种二氢苯并呋喃衍生物，并具有优异的非对映选择性。放大反应和产物的进一步衍生化效果良好，展示了当前反应在有机合成中的应用潜力。