(1R)-7,7-dimethyl-2-azabicyclo[4.1.1]octan-3-one | 87295-19-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (1R)-7,7-dimethyl-2-azabicyclo[4.1.1]octan-3-one
• 英文别名: (1R,6S)-7,7-dimethyl-2-azabicyclo[4.1.1]octan-3-one
• CAS: 87295-19-0
• 化学式: C₉H₁₅NO
• 分子量: 153.224
• InChiKey: QWIDXVHOGOXFLU-NKWVEPMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  3.0
• 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：

  (1R)-7,7-dimethyl-2-azabicyclo[4.1.1]octan-3-one 在 sodium nitrite 作用下， 以 甲醇 、 乙酸酐 为溶剂， 生成 (1S,2S)-1-(1-methoxy-1-methyl)ethyl-2-(2-methoxycarbonyl)ethylcyclopropane
  参考文献：
  名称：

  CHIRALITY TRANSFER DURING CYCLOBUTYL–CYCLOPROPYLMETHYL–HOMOALLYL CATION REARRANGEMENT AND SYNTHESIS OF (−)-ELDANOLIDE

  摘要：

  (3R)-2,2-二甲基-3-(2-甲氧羰基)乙基环丁基阳离子重新排列后得到 (1S,2S)-1-(1-甲氧基-1-甲基)乙基-2-(2-甲氧羰基)乙基环丙烷。后者转化为(4R)-4-(3-甲基丁-2-烯基)-4-丁内酯，手性转移程度很高。γ-内酯被转化成(-)-eldanolide，这是一种非洲甘蔗螟虫翅腺信息素的反式。

  DOI：

  10.1246/cl.1983.1245
• 作为产物：
  描述：

  beta-pinene 在 吡啶 、 盐酸羟胺 、 臭氧 、 对甲苯磺酰氯 作用下， 以 吡啶 、 甲醇 为溶剂， 生成 (1R)-7,7-dimethyl-2-azabicyclo[4.1.1]octan-3-one
  参考文献：
  名称：

  CHIRALITY TRANSFER DURING CYCLOBUTYL–CYCLOPROPYLMETHYL–HOMOALLYL CATION REARRANGEMENT AND SYNTHESIS OF (−)-ELDANOLIDE

  摘要：

  (3R)-2,2-二甲基-3-(2-甲氧羰基)乙基环丁基阳离子重新排列后得到 (1S,2S)-1-(1-甲氧基-1-甲基)乙基-2-(2-甲氧羰基)乙基环丙烷。后者转化为(4R)-4-(3-甲基丁-2-烯基)-4-丁内酯，手性转移程度很高。γ-内酯被转化成(-)-eldanolide，这是一种非洲甘蔗螟虫翅腺信息素的反式。

  DOI：

  10.1246/cl.1983.1245

文献信息

• Sustainable terpene-based polyamides <i>via</i> anionic polymerization of a pinene-derived lactam
  作者：Malte Winnacker、Jacob Sag

  DOI：10.1039/c7cc08266e

  日期：——

  A sustainable lactam, which is derived from the renewable terpene β-pinene, is converted to polyamides via a convenient anionic ring-opening polymerization (ROP), which can be easily handled without the use of a costly catalyst. The resulting polyamides have prosperous thermal properties, which enable their future use as high-performance polymers.

  衍生自可再生萜烯β-pine烯的可持续内酰胺通过便利的阴离子开环聚合（ROP）转化为聚酰胺，无需使用昂贵的催化剂即可轻松处理。所得聚酰胺具有良好的热性能，使其能够将来用作高性能聚合物。
• Guest/Host Relationships in the Synthesis of the Novel Cage-Based Zeolites SSZ-35, SSZ-36, and SSZ-39
  作者：Paul Wagner、Yumi Nakagawa、Greg S. Lee、Mark E. Davis、Saleh Elomari、Ronald C. Medrud、S. I. Zones

  DOI：10.1021/ja990722u

  日期：2000.1.1

  Here, we report the synthesis and structure of three high-silica molecular sieves, SSZ-35, SSZ-36, and SSZ-39, that are prepared from a library of 37 different cyclic and polycyclic quaternized amine molecules that are used as structure-directing agents (SDAs). The size and shape of the quaternized amine molecules are purposely designed in order to obtain novel zeolite structures, and the synthesis of these molecules is presented. The selectivity for the three molecular sieve phases is found to depend on both the SDA and the degree of heteroatom lattice substitution of Al3+ or B3+ in the silicate framework. Molecular modeling is utilized to probe the effects of the nonbonded SDA/zeolite-framework interaction energy on the selectivity for the observed molecular sieve phase. The Rietveld refinement of the powder X-ray data confirms the structure of the SSZ-39 zeolite to be isomorphous with the aluminophosphate molecular sieve, SAPO-LS (AEI). The structure of SSZ-36 is found to possess a range of fault probabilities between the two-dimensional channel system, end-member polymorphs, ITQ-3 and RUB-13 (International Zeolite Association Codes ITE and RTH, respectively). The SSZ-35 structure is reported to contain a one-dimensional pore system possessing stacked cages circumscribed by alternating rings of 10 and 18 tetrahedral atoms (10- and 18-membered rings).
• Synthesis and Antiviral and Cytostatic Activities of Carbocyclic Nucleosides Incorporating a Modified Cyclobutane Ring
  作者：M. José Figueira、J. Manuel Blanco、Olga Caamaño、Franco Fernández、Xerardo García-Mera、Carmen López、Graciela Andrei、Robert Snoeck、Elisabeth Padalko、Johan Neyts、Jan Balzarini、Erik De Clercq

  DOI：10.1002/(sici)1521-4184(199910)332:10<348::aid-ardp348>3.0.co;2-h

  日期：1999.10

  The new carbocyclic nucleosides were prepared by constructing a guanine (compounds 3, 5) or 8-azaguanine (compounds 4, 6, and 7) base on the amino group of (1'S, 3'R)-3-(3'-amino-2', 2'-di-methylcyclobutyl) propan-1-ol (8), and their activities against a variety of viruses and tumor cell lines were determined. Only compounds 3 and 7 showed a detectable activity at subtoxic concentrations against some viruses tested.
• CHIRALITY TRANSFER DURING CYCLOBUTYL–CYCLOPROPYLMETHYL–HOMOALLYL CATION REARRANGEMENT AND SYNTHESIS OF (−)-ELDANOLIDE
  作者：Yasushi Yokoyama、Masatoshi Yunokihara

  DOI：10.1246/cl.1983.1245

  日期：1983.8.5

  The (3R)-2,2-dimethyl-3-(2-methoxycarbonyl)ethylcyclobutyl cation rearranged to give (1S,2S)-1-(1-methoxy-1-methyl)ethyl-2-(2-methoxycarbonyl)ethylcyclopropane. The latter was transformed into (4R)-4-(3-methylbut-2-enyl)-4-butyrolactone with a high degree of chirality transfer. The γ-lactone was converted into (−)-eldanolide, an antipode of the wing gland pheromone of an African sugar-cane borer.

  (3R)-2,2-二甲基-3-(2-甲氧羰基)乙基环丁基阳离子重新排列后得到 (1S,2S)-1-(1-甲氧基-1-甲基)乙基-2-(2-甲氧羰基)乙基环丙烷。后者转化为(4R)-4-(3-甲基丁-2-烯基)-4-丁内酯，手性转移程度很高。γ-内酯被转化成(-)-eldanolide，这是一种非洲甘蔗螟虫翅腺信息素的反式。