3-氧代-1,3-二氢-2-苯并呋喃-1-甲酰氯 | 129881-51-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: 3-氧代-1,3-二氢-2-苯并呋喃-1-甲酰氯
• 英文名称: acid chloride of 1-oxo-1,3-dihydroisobenzofuran-3-carboxylic acid
• 英文别名: 3-oxo-1,3-dihydroisobenzofuran-1-carbonyl chloride；3-Oxo-1,3-dihydro-2-benzofuran-1-carbonyl chloride；3-oxo-1H-2-benzofuran-1-carbonyl chloride
• CAS: 129881-51-2；75724-95-7
• 化学式: C₉H₅ClO₃
• 分子量: 196.59
• InChiKey: XYKAJXOSGYGAMQ-UHFFFAOYSA-N

物化性质

• 沸点：
  345.8±42.0 °C(Predicted)
• 密度：
  1.487±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-氧代-1,3-二氢-2-苯并呋喃-1-甲酰氯 在 吡啶 、 PPA 、 Polyphosphoric acid (PPA) 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 4-(3-oxo-1,3-dihydroisobenzofuran-1-yl)-7-methoxyquinazolin-2(1H)-one
  参考文献：
  名称：

  Heinicke, Grant; Hung, Tran V.; Prager, Rolf H., Australian Journal of Chemistry, 1984, vol. 37, # 4, p. 831 - 844

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(羧基羰基)苯甲酸 在 sodium tetrahydroborate 、 氯化亚砜 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 3-氧代-1,3-二氢-2-苯并呋喃-1-甲酰氯
  参考文献：
  名称：

  Bhatt, M. Vivekananda; El Ashry, Shaker H.; Somayaji, Vishwanatha, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1980, vol. 19, # 6, p. 473 - 486

  摘要：

  DOI：

文献信息

• The Chemistry of Phthalide-3-carboxylic Acid. VII. Reaction With Isoquinoline Derivatives
  作者：C Donati、TV Hung、RH Prager

  DOI：10.1071/ch9900375

  日期：——

  Phthalide-3-carboxylic acid has been decarboxylated in the presence of isoquinoline, 1-chloroisoquinoline and isoquinoline N-oxides to give low yields of compounds resulting from alkylation of the isoquinoline heterocycle at C1 with a phthalidyl group. Attempted Barton decarboxylation-alkylation in the presence of isoquinolinium salts was unsuccessful.

  酞-3-羧酸在异喹啉、1-氯异喹啉和异喹啉 N-氧化物存在下进行脱羧反应，得到的化合物产率很低，这些化合物是异喹啉杂环在 C1 处与酞酰基发生烷基化反应而产生的。尝试在异喹啉鎓盐存在下进行巴顿脱羧-烷基化反应并不成功。
• Direct asymmetric Mannich reaction of phthalides: facile access to chiral substituted isoquinolines and isoquinolinones
  作者：Jie Luo、Haifei Wang、Fangrui Zhong、Jacek Kwiatkowski、Li-Wen Xu、Yixin Lu

  DOI：10.1039/c2cc31439h

  日期：——

  The first Mannich reaction employing phthalides using a quinidine-based multifunctional catalyst has been developed. The reported method led to the synthesis of 3,3-disubstituted phthalide derivatives in excellent yields, with good diastereo- and enantioselectivities. Convenient synthesis of chiral isoquinolinones and isoquinolines has also been demonstrated.

  首次利用基于奎尼丁的多功能催化剂进行邻苯二甲酸内酯的Mannich反应已被开发。所报道的方法合成了3,3-二取代的邻苯二甲酸内酯衍生物，产率极高，且具有良好的非对映选择性和对映选择性。此外，便捷合成手性异喹啉酮和异喹啉的示例也已得到证明。
• Process for the preparation of 5-cyanophthalide starting from 5-carboxyphthalide
  申请人：Adorkem Technology SpA

  公开号：EP1777221A1

  公开（公告）日：2007-04-25

  A new process is clescribed for obtaining 5-cyanophthalide, which is an intermediate used for the synthesis of citalopram and its active enantiomer S(+) citalopram, both of which are known active ingredients commonly used for treating depression. The process starts from 5-carboxyphthalide which is converted into the corresponding acylochloride. The latter is reacted with hydroxylamine to give the corresponding hydroxamyl phthalide which is subsequently subjected to a dehydration reaction to give 5-cyanophthalide.

  一种新的制备5-氰基邻苯二甲酸酰亚胺的工艺被描述，该化合物是合成舒必利和其活性对映体S（+）舒必利的中间体，两者均为治疗抑郁症常用的活性成分。该工艺从5-羧基邻苯二甲酸开始，将其转化为相应的酰氯化合物。然后将酰氯化合物与羟胺反应，得到相应的羟肟基邻苯二甲酸酰亚胺，随后进行脱水反应，得到5-氰基邻苯二甲酸酰亚胺。
• Highly Enantioselective Regiodivergent Allylic Alkylations of MBH Carbonates with Phthalides
  作者：Fangrui Zhong、Jie Luo、Guo-Ying Chen、Xiaowei Dou、Yixin Lu

  DOI：10.1021/ja303115m

  日期：2012.6.20

  Phthalides were used for the first time in the allylic alkylation reactions with MBH carbonates for the creation of chiral 3,3-disubstituted phthalides. Highly enantioselective regiodivergent synthesis of gamma-selective or beta-selective allylic alkylation products was achieved by employing bifunctional chiral phosphines or multifunctional tertiary amine-thioureas as the catalyst, respectively. It was demonstrated that proper selection of catalysts and reaction conditions would differentiate an S(N)2'-S(N)2' pathway and an addition-elimination process, yielding different regioisomers of the allylic alkylation products in a highly enantiomerically pure form.
• DONATI, COSIMO;HUNG, TRAN V.;PRAGER, ROLF H., AUSTRAL. J. CHEM., 43,(1990) N, C. 375-381
  作者：DONATI, COSIMO、HUNG, TRAN V.、PRAGER, ROLF H.

  DOI：——

  日期：——