(4-chlorophenyl)(2,3-dihydro-1,4-benzodioxin-6-yl)methanol | 775350-97-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: (4-chlorophenyl)(2,3-dihydro-1,4-benzodioxin-6-yl)methanol
• 英文别名: (4-chlorophenyl)-(2,3-dihydro-1,4-benzodioxin-6-yl)methanol
• CAS: 775350-97-5
• 化学式: C₁₅H₁₃ClO₃
• 分子量: 276.719
• InChiKey: MYYAIPPMTMDSMS-UHFFFAOYSA-N

物化性质

• 沸点：
  433.1±45.0 °C(Predicted)
• 密度：
  1.330±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  (4-chlorophenyl)(2,3-dihydro-1,4-benzodioxin-6-yl)methanol 在 六甲基磷酰三胺 、 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 、 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：

  (4-氯苯基)(2,3-二氢-1,4-苯并二氧杂环己-6-基)甲酮 在 sodium tetrahydroborate 作用下， 以87%的产率得到(4-chlorophenyl)(2,3-dihydro-1,4-benzodioxin-6-yl)methanol
  参考文献：
  名称：

  Hydrochloric acid as an efficient catalyst for intermolecular condensation of alcohols. A simple and highly efficient synthesis of unsymmetrical ethers from benzylic alcohols and alkanols

  摘要：

  Benzylic alcohols and diarylmethanols with electron-donating substituents in the aromatic ring reacted with aliphatic alcohols in the presence of a catalytic amount of HCl to give the corresponding alkyl arylmethyl ethers. The reactivity of diarylmethanols in the intermolecular dehydration depended on the nature of substituents in the aromatic rings and structure of aliphatic alcohol.

  DOI：

  10.1134/s107042801509002x

文献信息

• Hydrochloric acid as an efficient catalyst for intermolecular condensation of alcohols. A simple and highly efficient synthesis of unsymmetrical ethers from benzylic alcohols and alkanols
  作者：S. S. Mochalov、A. N. Fedotov、E. V. Trofimova、N. S. Zefirov

  DOI：10.1134/s107042801509002x

  日期：2015.9

  Benzylic alcohols and diarylmethanols with electron-donating substituents in the aromatic ring reacted with aliphatic alcohols in the presence of a catalytic amount of HCl to give the corresponding alkyl arylmethyl ethers. The reactivity of diarylmethanols in the intermolecular dehydration depended on the nature of substituents in the aromatic rings and structure of aliphatic alcohol.
• Discovery of L-791,943: A potent, selective, non emetic and orally active phosphodiesterase-4 inhibitor
  作者：Daniel Guay、Pierre Hamel、Marc Blouin、Christine Brideau、Chi Chung Chan、Nathalie Chauret、Yves Ducharme、Zheng Huang、Mario Girard、Tom R. Jones、France Laliberté、Paul Masson、Malia McAuliffe、Hanna Piechuta、José Silva、Robert N. Young、Yves Girard

  DOI：10.1016/s0960-894x(02)00190-7

  日期：2002.6

  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.
• Synthesis of symmetrical α-alkyl- and α-arylalkylbenzyl and diarylmethyl ethers by HCl-catalyzed intermolecular dehydration
  作者：S. S. Mochalov、A. N. Fedotov、E. V. Trofimova、N. S. Zefirov

  DOI：10.1134/s1070428017100050

  日期：2017.10

  alpha-Alkyl-, alpha-arylalkyl-, and alpha-aryl-substituted benzyl alcohols were converted into the corresponding symmetrical dibenzyl ethers in the presence of a catalytic amount of 10% aqueous HCl both in methylene chloride and under solvent-free conditions. Analogous reactions in dioxane and on heating afforded mainly the corresponding arylalkenes, whereas symmetrical dibenzyl ethers were formed as minor products.