2,2-bis-(3-chloro-propyl)-[1,3]dioxolane | 36823-78-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-bis-(3-chloro-propyl)-[1,3]dioxolane
• 英文别名: 2,2-Di-(3-chlor-propyl)-1,3-dioxolan；1,7-Dichlor-4-aethylendioxy-heptan；2,2-Bis(3-chloropropyl)-1,3-dioxolane
• CAS: 36823-78-6
• 化学式: C₉H₁₆Cl₂O₂
• 分子量: 227.131
• InChiKey: VKEVDJLCILOSIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2-bis-(3-chloro-propyl)-[1,3]dioxolane 在 四丁基氢氧化铵 、 四丁基碘化铵 、 sodium carbonate 、 苯硫酚 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙腈 为溶剂， 生成 1,4-Dioxa-9-aza-spiro<4.7>dodecan
  参考文献：
  名称：

  A synthetic approach to the actinophyllic acid molecular architecture

  摘要：

  Compounds 3a and 3b with the 1-azabicyclo[4.2.1]nonane ring system present in actinophyllic acid, have been synthesized. The method involves the intramolecular acid induced cyclization of the azafulvene 7 (formed between indole-3-carbaldehyde 5 and the azocan-5-one ethyleneketal 4b) into 3b in 48-60% yield as the key reaction. X-ray analyses of 3a and 3b showed they have the 'wrong' stereochemistry (indole-anti to the 7-member ring) for its use as a potential intermediate in an eventual synthesis of actinophyllic acid 1. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.02.050

文献信息

• The stereochemistry of spiropiperidine cyclizations (histrionicotoxin, part I)
  作者：Micheal Glanzmann、Chatchanok Karalai、Bernd Ostersehlt、Uwe Schön、Christiane Frese、Ekkehard Winterfeldt

  DOI：10.1016/0040-4020(82)85007-2

  日期：1982.1

  The spirocyclization of straingt-chain triketo-intermediates, similar to possible biogenetic precursors of histrionicotoxin, is shown to be stereoselective, generating the non-natural configuration at C-2. Aiming at an sp2-center in this position, triketo-brassylic ester was treated with ammonia at room temperature and was shown to cleanly and efficiently yield a spiroketone.

  类似于组蛋白毒素的可能的生物遗传前体，应变三链三酮中间产物的螺环化被证明是立体选择性的，在C-2处产生非天然构型。瞄准该位置的sp 2-中心，在室温下用氨处理三酮基-芥子酸酯，并显示其清洁有效地产生了螺酮。
• GLANZMANN, M.;KARALAI, C.;OSTERSEHLT, B.;SCHOEN, U.;FRESE, C.;WINTERFELDT+, TETRAHEDRON, 1982, 38, N 18, 2805-2810
  作者：GLANZMANN, M.、KARALAI, C.、OSTERSEHLT, B.、SCHOEN, U.、FRESE, C.、WINTERFELDT+

  DOI：——

  日期：——
• A synthetic approach to the actinophyllic acid molecular architecture
  作者：Ivann Zaragoza Galicia、Luis A. Maldonado

  DOI：10.1016/j.tetlet.2013.02.050

  日期：2013.4

  Compounds 3a and 3b with the 1-azabicyclo[4.2.1]nonane ring system present in actinophyllic acid, have been synthesized. The method involves the intramolecular acid induced cyclization of the azafulvene 7 (formed between indole-3-carbaldehyde 5 and the azocan-5-one ethyleneketal 4b) into 3b in 48-60% yield as the key reaction. X-ray analyses of 3a and 3b showed they have the 'wrong' stereochemistry (indole-anti to the 7-member ring) for its use as a potential intermediate in an eventual synthesis of actinophyllic acid 1. (C) 2013 Elsevier Ltd. All rights reserved.