Benzo[1,3]dioxol-5-yl-(4-chloro-phenyl)-methanol | 775350-95-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: Benzo[1,3]dioxol-5-yl-(4-chloro-phenyl)-methanol
• 英文别名: 1,3-Benzodioxol-5-yl-(4-chlorophenyl)methanol
• CAS: 775350-95-3
• 化学式: C₁₄H₁₁ClO₃
• mdl: MFCD16334842
• 分子量: 262.693
• InChiKey: WJBHVMFTWUOPHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Benzo[1,3]dioxol-5-yl-(4-chloro-phenyl)-methanol 在 六甲基磷酰三胺 、 sodium hydroxide 、 氯化亚砜 、 双(三甲基硅烷基)氨基钾 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醇 、 苯 为溶剂， 生成
  参考文献：
  名称：

  Discovery of L-791,943: A potent, selective, non emetic and orally active phosphodiesterase-4 inhibitor

  摘要：

  Structure-activity relationship studies directed toward improving the potency and metabolic stability of CDP-840 (3) resulted in the discovery of L-791,943 (1 In) as a potent (HWB TNF-alpha = 0.67 muM) and orally active phosphodiesterase type 4 (PDE4) inhibitor. This compound, which bears a stable bis-difluoromethoxy catechol and a pendant hexafluorocarbinol, exhibited a long half-life in rat and in squirrel monkey. It is well tolerated in ferret with an emetic threshold greater than 30 mg/kg (po) and was found to be active in the ovalbumin-induced bronchoconstriction model in guinea pig and in the ascaris-induced bronchoconstriction models in sheep and squirrel monkey. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00190-7
• 作为产物：
  描述：

  3,4-二羟基苯甲醛 在 caesium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 Benzo[1,3]dioxol-5-yl-(4-chloro-phenyl)-methanol
  参考文献：
  名称：

  Discovery of L-791,943: A potent, selective, non emetic and orally active phosphodiesterase-4 inhibitor

  摘要：

  Structure-activity relationship studies directed toward improving the potency and metabolic stability of CDP-840 (3) resulted in the discovery of L-791,943 (1 In) as a potent (HWB TNF-alpha = 0.67 muM) and orally active phosphodiesterase type 4 (PDE4) inhibitor. This compound, which bears a stable bis-difluoromethoxy catechol and a pendant hexafluorocarbinol, exhibited a long half-life in rat and in squirrel monkey. It is well tolerated in ferret with an emetic threshold greater than 30 mg/kg (po) and was found to be active in the ovalbumin-induced bronchoconstriction model in guinea pig and in the ascaris-induced bronchoconstriction models in sheep and squirrel monkey. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00190-7

文献信息

• Employing Arynes for the Generation of Aryl Anion Equivalents and Subsequent Reaction with Aldehydes
  作者：Rahul N. Gaykar、Anup Bhunia、Akkattu T. Biju

  DOI：10.1021/acs.joc.8b01549

  日期：2018.9.21

  a new synthetic strategy is demonstrated, where arynes are converted into aryl anion equivalents by treatment with phosphines and a base. The addition of phosphines to arynes form the phosphonium salts, which in the presence of a carbonate base generates the aryl anion equivalent. Subsequent addition of the aryl anions with aldehydes afforded the secondary alcohols.

  芳烃是高反应性的中间体，可用于各种X–H键（X = O，N，S等）的亲电芳基化。本文中，证明了一种新的合成策略，其中通过用膦和碱处理将芳烃转化为芳基阴离子当量。将膦类添加到芳烃中形成form盐，其在碳酸酯碱的存在下产生芳基阴离子当量。随后将芳基阴离子与醛加成，得到仲醇。