rac-(2-amino-phenyl)-(2-chloro-phenyl)-methanol | 74067-43-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: rac-(2-amino-phenyl)-(2-chloro-phenyl)-methanol
• 英文别名: (2-aminophenyl)(2-chlorophenyl)methanol；(2-aminophenyl)-(2-chlorophenyl)methanol
• CAS: 74067-43-9
• 化学式: C₁₃H₁₂ClNO
• 分子量: 233.697
• InChiKey: XVXUHJQJJQGPRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  rac-(2-amino-phenyl)-(2-chloro-phenyl)-methanol 在 sodium hydroxide 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 [(2-Amino-phenyl)-(2-chloro-phenyl)-methylsulfanyl]-acetic acid
  参考文献：
  名称：

  Efficient Syntheses of Benzothiazepines as Antagonists for the Mitochondrial Sodium−Calcium Exchanger:  Potential Therapeutics for Type II Diabetes

  摘要：

  Type II diabetes mellitus is a chronic metabolic disorder that can lead to serious cardiovascular, renal, neurologic, and retinal complications. While several drugs are currently prescribed to treat type II diabetes, their efficacy is limited by mechanism-related side effects (weight gain, hypoglycemia, gastrointestinal distress), inadequate efficacy for use as monotherapy, and the development of tolerance to the agents. Consequently, combination therapies are frequently employed to effectively regulate blood glucose levels. We have focused on the mitochondrial sodium-calcium exchanger (mNCE) as a novel target for diabetes drug discovery. We have proposed that inhibition of the mNCE can be used to regulate calcium flux across the mitochondrial membrane, thereby enhancing mitochondrial oxidative metabolism, which in turn enhances glucose-stimulated insulin secretion (GSIS) in the pancreatic beta-cell. In this paper, we report the facile synthesis of benzothiazepines and derivatives by S-alkylation using 2-aminobenzhydrols. The syntheses of other bicyclic analogues based on benzothiazepine, benzothiazecine, benzodiazecine, and benzodiazepine templates are also described. These compounds have been evaluated for their inhibition of mNCE activity, and the results from the structure-activity relationship (SAR) studies are discussed.

  DOI：

  10.1021/jo020446t
• 作为产物：
  描述：

  2-氨基-2-氯苯甲酮 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 rac-(2-amino-phenyl)-(2-chloro-phenyl)-methanol
  参考文献：
  名称：

  Rizzetto, Elisa; Castellano; Florio, Pharmazie, 2006, vol. 61, # 6, p. 505 - 510

  摘要：

  DOI：

文献信息

• Room‐Temperature, Metal‐Free, and One‐Pot Preparation of 2 <i>H</i> ‐Indazoles through a Mills Reaction and Cyclization Sequence
  作者：Masaru Kondo、Shinobu Takizawa、Yuzhao Jiang、Hiroaki Sasai

  DOI：10.1002/chem.201902242

  日期：2019.7.25

  The Mills reaction and cyclization of readily available 2‐aminobenzyl alcohols and nitrosobenzenes using thionyl bromide provided 2H‐indazoles in up to 88 % yields. In the metal‐free process, acetic acid played a crucial role for the both Mills reaction and cyclization. A brominated 2H‐indazole could also be obtained through the one‐pot sequence.

  使用亚硫酰溴进行的Mills反应和易于获得的2-氨基苄醇和亚硝基苯的环化反应可提供高达88％收率的2 H-吲唑。在无金属过程中，乙酸对于Mills反应和环化都起着至关重要的作用。也可以通过一锅法获得溴化的2 H-吲唑。
• Aminohaloborane in organic synthesis. VIII. A one-step synthesis of 2-Aminobenzhydrols from anilines
  作者：Tatsuo Toyoda、Kazuyuki Sasakura、Tsutomu Sugasawa

  DOI：10.1016/s0040-4039(00)71405-5

  日期：1980.1