3-氧代-1-噁-7-氮杂螺[4.5]癸烷-7-羧酸叔丁酯 | 1160246-89-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 中文名称: 3-氧代-1-噁-7-氮杂螺[4.5]癸烷-7-羧酸叔丁酯
• 中文别名: 3-氧代-1-氧代-氧杂-7-氮杂螺[4.5]癸烷-7-羧酸叔丁酯
• 英文名称: tert-butyl 3-oxo-1-oxa-7-azaspiro[4.5]decane-7-carboxylate
• 英文别名: 3-Oxo-1-oxa-7-aza-spiro[4.5]decane-7-carboxylic acid tert-butyl ester；tert-butyl 3-oxo-1-oxa-9-azaspiro[4.5]decane-9-carboxylate
• CAS: 1160246-89-8
• 化学式: C₁₃H₂₁NO₄
• 分子量: 255.314
• InChiKey: FYSJPKBXFXYASC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  3-氧代-1-噁-7-氮杂螺[4.5]癸烷-7-羧酸叔丁酯 在 叔丁基锂 、 对甲苯磺酰肼 作用下， 以 四氢呋喃 、 乙醇 、 正戊烷 为溶剂， 反应 22.5h， 生成 Tert-butyl 2-formyl-1-oxa-9-azaspiro[4.5]dec-2-ene-9-carboxylate
  参考文献：
  名称：

  Synthesis of a Family of Spirocyclic Scaffolds: Building Blocks for the Exploration of Chemical Space

  摘要：

  This report describes the preparation Of a series of 17 novel racemic spirocyclic scaffolds that are intended for the creation of compound libraries by parallel synthesis for biological screening. Each scaffold features two points of orthogonal diversification. The scaffolds are related to each other in four ways: (1) through stepwise changes in the size of the nitrogen-bearing ring; (2) through the oxidation state of the carbon-centered point of diversification; (3) through the relative stereochemical orientation of the two diversification sites in those members that are stereogenic; and (4) through the provision of both saturated and unsaturated versions of the furan ring in the scaffold series derived from 3-piperidone. The scaffolds provide incremental changes in the relative Orientation of the diversity components that would be introduced onto them. The scaffolds feature high sp(3) carbon content which is essential for the three-dimensional exploration Of chemical space. This characteristic is particularly evident in those members of this family that bear two stereocenters, i.e., the two series derived from 3-piperidone and 3-pyrrolidinone. In the series derived from 3-piperidone we were able to "split the difference" between the two diastereomers by preparation of their corresponding unsaturated version.

  DOI：

  10.1021/jo400738b
• 作为产物：
  描述：

  N-叔丁氧羰基-3-哌啶酮 在 正丁基锂 、 甲烷磺酸 、 3,5-二氯吡啶 N-氧化物 、 水 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 1,2-二氯乙烷 为溶剂， 反应 12.67h， 生成 3-氧代-1-噁-7-氮杂螺[4.5]癸烷-7-羧酸叔丁酯
  参考文献：
  名称：

  Skeletal Diversification via Heteroatom Linkage Control: Preparation of Bicyclic and Spirocyclic Scaffolds from N-Substituted Homopropargyl Alcohols

  摘要：

  The discovery and application of a new branching pathway synthesis strategy that rapidly produces skeletally diverse scaffolds is described. Two different scaffold types, one a bicyclic iodo-vinylidene tertiary amine/tertiary alcohol and the other, a spirocyclic 3-furanone, are each obtained using a two-step sequence featuring a common first step. Both scaffold types lead to intermediates that can be orthogonally diversified using the same final components. One of the scaffold types was obtained in sufficiently high yield that it was immediately used to produce a 97 compound library.

  DOI：

  10.1021/jo400077m

文献信息

• Synthesis of a Family of Spirocyclic Scaffolds: Building Blocks for the Exploration of Chemical Space
  作者：Sarvesh Kumar、Paul D. Thornton、Thomas O. Painter、Prashi Jain、Jared Downard、Justin T. Douglas、Conrad Santini

  DOI：10.1021/jo400738b

  日期：2013.7.5

  This report describes the preparation Of a series of 17 novel racemic spirocyclic scaffolds that are intended for the creation of compound libraries by parallel synthesis for biological screening. Each scaffold features two points of orthogonal diversification. The scaffolds are related to each other in four ways: (1) through stepwise changes in the size of the nitrogen-bearing ring; (2) through the oxidation state of the carbon-centered point of diversification; (3) through the relative stereochemical orientation of the two diversification sites in those members that are stereogenic; and (4) through the provision of both saturated and unsaturated versions of the furan ring in the scaffold series derived from 3-piperidone. The scaffolds provide incremental changes in the relative Orientation of the diversity components that would be introduced onto them. The scaffolds feature high sp(3) carbon content which is essential for the three-dimensional exploration Of chemical space. This characteristic is particularly evident in those members of this family that bear two stereocenters, i.e., the two series derived from 3-piperidone and 3-pyrrolidinone. In the series derived from 3-piperidone we were able to "split the difference" between the two diastereomers by preparation of their corresponding unsaturated version.
• Skeletal Diversification via Heteroatom Linkage Control: Preparation of Bicyclic and Spirocyclic Scaffolds from N-Substituted Homopropargyl Alcohols
  作者：Thomas O. Painter、Jonathon R. Bunn、Frank J. Schoenen、Justin T. Douglas、Victor W. Day、Conrad Santini

  DOI：10.1021/jo400077m

  日期：2013.4.19

  The discovery and application of a new branching pathway synthesis strategy that rapidly produces skeletally diverse scaffolds is described. Two different scaffold types, one a bicyclic iodo-vinylidene tertiary amine/tertiary alcohol and the other, a spirocyclic 3-furanone, are each obtained using a two-step sequence featuring a common first step. Both scaffold types lead to intermediates that can be orthogonally diversified using the same final components. One of the scaffold types was obtained in sufficiently high yield that it was immediately used to produce a 97 compound library.