(3R)-5-chloro-8-methoxy-3-methyl-1-oxo-3,4-dihydro-1H-isochromene-7-carboxylic acid | 1421840-16-5

• 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: (3R)-5-chloro-8-methoxy-3-methyl-1-oxo-3,4-dihydro-1H-isochromene-7-carboxylic acid
• 英文别名: (3R)-5-chloro-8-methoxy-3-methyl-1-oxo-3,4-dihydroisochromene-7-carboxylic acid
• CAS: 1421840-16-5
• 化学式: C₁₂H₁₁ClO₅
• 分子量: 270.669
• InChiKey: COOKSONQFOLZSK-RXMQYKEDSA-N

物化性质

• 溶解度：
  可溶于二甲基亚砜、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R)-5-chloro-8-methoxy-3-methyl-1-oxo-3,4-dihydro-1H-isochromene-7-carboxylic acid 在 双氧水 、 三氯化硼 、 四氯化钛 、 silver nitrate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 39.0h， 生成 5-氯-8-羟基-3-甲基-1-氧代异色满-7-羧酸
  参考文献：
  名称：

  Efficient synthesis of (R)-ochratoxin alpha, the key precursor to the mycotoxin ochratoxin A

  摘要：

  Two new routes for the synthesis of enantiomerically pure ochratoxin alpha ((3R)-OT alpha) are presented, which is the key intermediate for the synthesis of ochratoxin A (OTA) by coupling reaction with the amino acid (L)-phenylalanine. The key step of both routes is the one pot directed ortho-metalation/alkylation/lactonization of unprotected and suitably functionalized aromatic carboxylic acids, using lithium tetramethylpiperidide (LIMP) and (R)-propylene oxide. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.11.123
• 作为产物：
  描述：

  5-氯间二甲苯-2,alpha,alpha'-三醇 在 potassium permanganate 、 2,2,6,6-tetramethylpiperidinyl-lithium 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 5.5h， 生成 (3R)-5-chloro-8-methoxy-3-methyl-1-oxo-3,4-dihydro-1H-isochromene-7-carboxylic acid
  参考文献：
  名称：

  Efficient synthesis of (R)-ochratoxin alpha, the key precursor to the mycotoxin ochratoxin A

  摘要：

  Two new routes for the synthesis of enantiomerically pure ochratoxin alpha ((3R)-OT alpha) are presented, which is the key intermediate for the synthesis of ochratoxin A (OTA) by coupling reaction with the amino acid (L)-phenylalanine. The key step of both routes is the one pot directed ortho-metalation/alkylation/lactonization of unprotected and suitably functionalized aromatic carboxylic acids, using lithium tetramethylpiperidide (LIMP) and (R)-propylene oxide. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.11.123

文献信息

• Efficient synthesis of (R)-ochratoxin alpha, the key precursor to the mycotoxin ochratoxin A
  作者：Cesar Antonio Lenz、Michael Rychlik

  DOI：10.1016/j.tetlet.2012.11.123

  日期：2013.2

  Two new routes for the synthesis of enantiomerically pure ochratoxin alpha ((3R)-OT alpha) are presented, which is the key intermediate for the synthesis of ochratoxin A (OTA) by coupling reaction with the amino acid (L)-phenylalanine. The key step of both routes is the one pot directed ortho-metalation/alkylation/lactonization of unprotected and suitably functionalized aromatic carboxylic acids, using lithium tetramethylpiperidide (LIMP) and (R)-propylene oxide. (C) 2012 Elsevier Ltd. All rights reserved.