5-Chloro-2-(2-methyl-[1,3]dioxolan-2-yl)-benzoic acid | 1027831-97-5

• 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: 5-Chloro-2-(2-methyl-[1,3]dioxolan-2-yl)-benzoic acid
• 英文别名: 5-Chloro-2-(2-methyl-1,3-dioxolan-2-yl)benzoic acid
• CAS: 1027831-97-5
• 化学式: C₁₁H₁₁ClO₄
• 分子量: 242.659
• InChiKey: IVXRAUUKRRMBDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-Chloro-2-(2-methyl-[1,3]dioxolan-2-yl)-benzoic acid 在 盐酸 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 6-chloro-3-methylisobenzofuran-1(3H)-one
  参考文献：
  名称：

  Lithiation of 2-(chloroaryl)-2-methyl-1,3-dioxolanes and application in synthesis of new ortho -functionalized acetophenone derivatives

  摘要：

  2-(4-Chlorophenyl)-2-methyl-1,3-dioxolane 2a was lithiated ortho to the ketal group by treatment with butyllithium in THF at 0degreesC. Related 2-aryl-2-methyl-1,3-dioxolanes possessing a chlorine substituent at the meta position of the aryl group 2b,c were lithiated with butyllithium in THF at -78degreesC at the position between the two directing groups. The lithio species thus generated were treated with various electrophiles to give ortho-functionalized acetophenone derivatives. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00391-5
• 作为产物：
  描述：

  对氯苯乙酮 在 正丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 3.0h， 生成 5-Chloro-2-(2-methyl-[1,3]dioxolan-2-yl)-benzoic acid
  参考文献：
  名称：

  Lithiation of 2-(chloroaryl)-2-methyl-1,3-dioxolanes and application in synthesis of new ortho -functionalized acetophenone derivatives

  摘要：

  2-(4-Chlorophenyl)-2-methyl-1,3-dioxolane 2a was lithiated ortho to the ketal group by treatment with butyllithium in THF at 0degreesC. Related 2-aryl-2-methyl-1,3-dioxolanes possessing a chlorine substituent at the meta position of the aryl group 2b,c were lithiated with butyllithium in THF at -78degreesC at the position between the two directing groups. The lithio species thus generated were treated with various electrophiles to give ortho-functionalized acetophenone derivatives. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00391-5

文献信息

• Lithiation of 2-aryl-2-methyl-1,3-dioxolanes with PMDTA-complexed butyllithium
  作者：Bálint Nyulasi、András Németh、Márta Porcs-Makkay、József Kupai、Gyula Lukács、Gyula Simig、Balázs Volk

  DOI：10.1016/j.tet.2016.11.072

  日期：2017.1

  The lithio species thus generated were carboxylated to benzoic acids. Lithiations with BuLi occurred regioselectively ortho to the ketal substituent. When using BuLi/PMDTA, a regiodivergent behavior has generally been found in the lithiations. However, in some cases a significant selectivity was observed, enabling the preparation of the main regioisomer, exhibiting a new substitution pattern, with reasonable

  氯和甲氧基取代的苯乙酮缩酮的用丁基锂锂（BuLi），并与金属化Ñ，Ñ，Ñ '，Ñ “，Ñ ” -五甲基络合丁基锂（丁基锂/ PMDTA）进行了研究。由此产生的锂硫基物质被羧化为苯甲酸。与丁基锂Lithiations发生区域选择性邻位的缩酮取代。使用BuLi / PMDTA时，通常在锂化中发现了区域发散行为。然而，在某些情况下，观察到显着的选择性，从而能够制备主要的区域异构体，并显示出新的取代模式，且产率合理。