1,2,3,5,6,7-hexahydroindolizine-8-carboxylic acid ethyl ester | 90407-59-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1,2,3,5,6,7-hexahydroindolizine-8-carboxylic acid ethyl ester
• 英文别名: ethyl 1,2,3,5,6,7-hexahydroindolidine-8-carboxylate；ethyl 1,2,3,5,6,7-hexahydroindolizine-8-carboxylate；8-carbethoxy-1,2,3,5,6,7-hexahydroindolizine；8-Indolizinecarboxylic acid, 1,2,3,5,6,7-hexahydro-, ethyl ester
• CAS: 90407-59-3
• 化学式: C₁₁H₁₇NO₂
• 分子量: 195.261
• InChiKey: ZXDNCDFCIYZDDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,2,3,5,6,7-hexahydroindolizine-8-carboxylic acid ethyl ester 生成 cis-Ethyl octahydroindolizine-8-carboxylate
  参考文献：
  名称：

  HADDAD, MANSOUR;CELERIER, JEAN PIERRE;HAVIARI, GJERGJ;LHOMMET, GERARD;DHT+, HETEROCYCLES, 31,(1990) N, C. 1251-1260

  摘要：

  DOI：
• 作为产物：
  描述：

  5-<1-(3-chloropropyl)-2-pyrrolidinylidene>-2,2-dimethyl-1,3-dioxane-4,6-dione 在 三氟化硼乙醚 、 sodium iodide 作用下， 以 乙腈 为溶剂， 生成 1,2,3,5,6,7-hexahydroindolizine-8-carboxylic acid ethyl ester
  参考文献：
  名称：

  Haddad, Mansour; Celerier, Jean Pierre; Haviari, Gjergj, Heterocycles, 1990, vol. 31, # 7, p. 1251 - 1260

  摘要：

  DOI：

文献信息

• An Efficient Sequential Reaction Process to Polysubstituted Indolizidines and Quinolizidines and Its Application to the Total Synthesis of Indolizidine 223A
  作者：Wei Zhu、Dapeng Dong、Xiaotao Pu、Dawei Ma

  DOI：10.1021/ol047476y

  日期：2005.2.1

  The reaction of iodides 1 with delta-chloropropylamines 5 in MeCN assisted with K2CO3 undergoes a sequential S(N)2/Michael addition/SN2/SN2 reaction process to give polysubstituted indolizidines and quinolizidines. Using this method, indolizidine 223A is synthesized from 2-ethyl-2-hexenoic acid in 12 linear steps and 14.5% overall yield. [Reaction: see text]

  碘化物1与δ-氯丙胺5在MeCN中辅以K2CO3的反应按顺序进行S（N）2 / Michael加成/ SN2 / SN2反应，得到多取代的吲哚并咪唑和喹喔啉。使用该方法，由吲哚并咪唑223A由2-乙基-2-己酸以12个线性步骤合成，并且总产率为14.5％。[反应：请参阅文字]
• New syntheses of (±)-tashiromine and (±)-epitashiromine via enaminone intermediates
  作者：Darren L Riley、Joseph P Michael、Charles B de Koning

  DOI：10.3762/bjoc.12.256

  日期：——

  The syntheses of the naturally occurring indolizidine alkaloid (±)-tashiromine and its unnatural epimer (±)-epitashiromine are demonstrated through the use of enaminone chemistry. The impact of various electron-withdrawing substituents at the C-8 position of the indolizidine core on the preparation of the bicyclic system is described.

  通过使用烯胺酮化学方法，演示了天然存在的吲哚啉生物碱(±)-太白胺和其非自然对映体(±)-表太白胺的合成。描述了在吲哚啉核心的C-8位置引入不同电子吸引取代基对双环系统制备的影响。
• Ring-Chain Tautomerism in Organic Synthesis:  Synthesis of Heterocyclic Enamines from a Novel and Practical Formal Ring Transformation Reaction of Lactones
  作者：Mei-Xiang Wang、Yong Liu、Hong-Yun Gao、Yan Zhang、Chu-Yi Yu、Zhi-Tang Huang、George W. J. Fleet

  DOI：10.1021/jo026560t

  日期：2003.4.1

  A novel approach to heterocyclic enamines has been developed from the formal ring transformation reaction of lactones. The synthesis comprises consecutive Reformatsky reaction of lactones and mesylation of the resulting mixture of ring-chain tautomers in a one-pot reaction, followed by cyclocondensation reaction with primary amines. The synthetic application of this method was demonstrated by a straightforward

  从内酯的正式环转化反应已经开发出一种杂环烯胺的新方法。合成包括内酯的连续Reformatsky反应和在单锅反应中将所得的环链互变异构体混合物进行甲磺酰化，然后与伯胺进行环缩合反应。该方法的合成应用是通过N-（3-溴丙基）-取代的烯胺中间体直接制备吲哚并立定化合物来证明的。在非常温和的条件下使用廉价且容易获得的材料和试剂使这种正式的环转化方法实用且可用于制备各种杂环烯胺，这些杂环烯胺是（多）羟基化生物碱衍生物的前体。
• A sequential reaction process to assemble polysubstituted indolizidines, quinolizidines and quinolizidine analogues
  作者：Guorong Cai、Wei Zhu、Dawei Ma

  DOI：10.1016/j.tet.2006.03.068

  日期：2006.6

  The omega-iodo-alpha,beta-alkynoates and their ketone, sulfone or phosphonate analogues react with delta-chloropropylamines in MeCN assisted with K2CO3 to undergo a sequential S(N)2/Michael addition/S(N)2/S(N)2 reaction process, giving polysubstituted indolizidines or quinolizidines in good to excellent yields. This sequential reaction process is also compatible with three other substituted alpha,beta-alkynoates, affording quinolizidine analogues in moderate to good yields. (c) 2006 Elsevier Ltd. All rights reserved.
• Chemoselective Intramolecular Alkylation of the Blaise Reaction Intermediates: Tandem One-Pot Synthesis of <i>exo</i>-Cyclic Enaminoesters and Their Applications toward the Synthesis of <i>N</i>-Heterocyclic Compounds
  作者：Ju Hyun Kim、Hyunik Shin、Sang-gi Lee

  DOI：10.1021/jo201964a

  日期：2012.2.3

  The intramolecular alkylative reactivity and N/C selectivity of the various Blaise reaction intermediates, which are formed from the reaction of the Reformatsky reagents with omega-chloroalkyl nitriles, did not reach the synthetic potential as an entry to exo-cyclic enaminoesters. To circumvent this issue, various additives were investigated, among which the addition of NaHMDS dramatically enhanced the reactivity and N/C selectivity. This modification provided a highly efficient route for the synthesis of various N-fused heterocyclic compounds, as it requires only two steps from nitriles.