(1S)-4,7,7-trimethyl-2-azabicyclo<2.2.1>heptan-3-one | 24326-88-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (1S)-4,7,7-trimethyl-2-azabicyclo<2.2.1>heptan-3-one
• 英文别名: (1S,4R)-4,7,7-trimethyl-2-azabicyclo[2.2.1]heptan-3-one
• CAS: 24326-88-3
• 化学式: C₉H₁₅NO
• 分子量: 153.224
• InChiKey: OSAYUIJRYXXRAG-RCOVLWMOSA-N

物化性质

• 沸点：
  265.1±9.0 °C(Predicted)
• 密度：
  1.015±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1S)-4,7,7-trimethyl-2-azabicyclo<2.2.1>heptan-3-one 在 甲基二氯化铝 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (1S,4R)-2-((1S,6S)-4,6-Dimethyl-cyclohex-3-enecarbonyl)-4,7,7-trimethyl-2-aza-bicyclo[2.2.1]heptan-3-one
  参考文献：
  名称：

  Toward the development of a general chiral auxiliary. 1. Preparation of a new class of camphor lactam imides and their application to the construction of quaternary centers via Diels-Alder cycloaddition.

  摘要：

  DOI：

  10.1021/ja00032a051
• 作为产物：
  描述：

  (1S)-2.2.3t-trimethyl-1r-carbamoyl-cyclopentane-carboxylic acid-(3c)-methyl ester 在 锂硼氢 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 7.5h， 生成 (1S)-4,7,7-trimethyl-2-azabicyclo<2.2.1>heptan-3-one
  参考文献：
  名称：

  SYNTHESIS OF (1R,3S)-3-AMINO-1,2,2-TRIMETHYLCYCLOPENTYLMETHANOL

  摘要：

  DOI：

  10.1080/00304949809355261

文献信息

• The Development of a Convergent and Efficient Enantioselective Synthesis of the Bengamides via a Common Polyol Intermediate
  作者：Robert K. Boeckman, Jr.、Tammy J. Clark、Brian C. Shook

  DOI：10.1002/hlca.200290026

  日期：2002.12

  the bengamide family of antitumor agents from a common polyol thioester is described. Consecutive aldol condensations afford the protected polyol thioester side chain suitable for coupling to the bengamides. A novel chiral-phase-transfer-catalyzed enantioselective alkylation affords the properly functionalized caprolactams required for the synthesis of more-complex members of the bengamide family. Use

  描述了一种从普通的多元醇硫酯到抗肿瘤剂苯甲酰胺家族的有效，通用的合成途径。连续的醛醇缩合得到适合于偶联至苯甲酰胺的被保护的多元醇硫酯侧链。一种新颖的手性相转移催化的对映选择性烷基化提供了合成苯甲酰胺家族中更复杂成员所需的适当官能化的己内酰胺。与对映选择性的羟醛缩合所需的硼路易斯酸相容的甲基2-萘基醚保护基的使用，可直接获得所有的苯甲酰胺。
• Facile Preparation and Functionalization of Chiral Stabilized Ylides from Common Chiral Auxiliaries Using Triphenyl- phosphoranylideneketene (the Bestmann Ylide) and Their Use in Wittig Reactions
  作者：Robert K. Boeckman,、Xinyi Song、Joseph E. Pero

  DOI：10.1021/jo061732y

  日期：2006.11.1

  Camphor-derived lactams and other related chiral controllers have been found to react with the Bestmann ylide (triphenyl-phosphoranylideneketene) upon heating in toluene. The resulting parent ylides provide convenient access to a structurally diverse set of chiral stabilized ylides via functionalization. The utility of these chiral ylides for Wittig reactions has been briefly investigated and the effects of alpha-substitution noted.
• Toward the Development of a General Chiral Auxiliary. 9. Highly Diastereoselective Alkylations and Acylations to Form Tertiary and Quaternary Centers
  作者：Robert K. Boeckman,、Debra J. Boehmler、Rhonda A. Musselman

  DOI：10.1021/ol016738i

  日期：2001.11.1

  [GRAPHICS]Enolates of a new camphor-derived lactam auxiliary are shown to monoalkylate with very high diastereoselectivity. A second alkylation occurs with reactive alkylating agents to afford quaternary centers also with high diastereoselectivity, In accord with a proposed model for diastereoselection, lithium and sodium enolates provide products with an opposite sense of asymmetric induction.
• Copper Sulfate-Pentahydrate-1,10-Phenanthroline Catalyzed Amidations of Alkynyl Bromides. Synthesis of Heteroaromatic Amine Substituted Ynamides
  作者：Yanshi Zhang、Richard P. Hsung、Michael R. Tracey、Kimberly C. M. Kurtz、Eymi L. Vera

  DOI：10.1021/ol049827e

  日期：2004.4.1

  A practical cross-coupling of amides with alkynyl bromides using catalytic CuSO(4)(.)5H(2)O and 1,10-phenanthroline is described here. This catalytic protocol is more environmentally friendly than the use of CuCN or copper halides and provides a general entry for syntheses of ynamides including various new sulfonyl and heteroaromatic amine substituted ynamides. Given the interest in ynamides, this N-alkynylation of amides should be significant for the future of ynamides in organic synthesis.
• A Copper-Catalyzed C−N Bond Formation Involving sp-Hybridized Carbons. A Direct Entry to Chiral Ynamides via N-Alkynylation of Amides
  作者：Michael O. Frederick、Jason A. Mulder、Michael R. Tracey、Richard P. Hsung、Jian Huang、Kimberly C. M. Kurtz、Lichun Shen、Christopher J. Douglas

  DOI：10.1021/ja021304j

  日期：2003.3.1

  A copper-catalyzed new C-N bond formation involving a sp-hybridized carbon is described here leading to a facile entry for syntheses of chiral ynamides. This direct N-alkynylation of amides should have a significant impact on the future development of synthetic methodologies employing ynamides.