3,7,7-trimethylbicyclo<4.1.0>hept-2-en-4-one oxime | 37876-55-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3,7,7-trimethylbicyclo<4.1.0>hept-2-en-4-one oxime
• 英文别名: (+)-(1S,6R)-car-2-en-4-one (E)-oxime；(1S,6R)-car-2-en-4one E-oxime；2-caren-4-one oxime；(NE)-N-[(1R,6S)-4,7,7-trimethyl-3-bicyclo[4.1.0]hept-4-enylidene]hydroxylamine
• CAS: 37876-55-4
• 化学式: C₁₀H₁₅NO
• 分子量: 165.235
• InChiKey: CVDOTKRHZGLHNK-WGRRCAOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,7,7-trimethylbicyclo<4.1.0>hept-2-en-4-one oxime 在 sodium nitrite 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 168.0h， 以62%的产率得到(+)-(1S,6R)-2-nitrocar-2-en-4-one (E)-oxime
  参考文献：
  名称：

  摘要：

  Using a number of cyclic alpha,beta-unsaturated oximes of the terpene series and sonic Simplest model compounds as examples, unsaturated oximes bearing a hydrogen atom it the beta-carbon atom were demonstrated to be converted into beta-hydroxyiminonitroalkenes under the action of sodium nitrite and acetic acid in methanol. In the case of the introduction of an alkyl substituent at the terminal carbon atom of the diene C=C-C=NOH fragment, the reaction performed under the same conditions gave rise exclusively to conjugated ketone (a deoximation product).

  DOI：

  10.1023/a:1012785007135
• 作为产物：
  描述：

  3-carene-4-nitroso-3-chloride 以 氯仿 为溶剂， 反应 48.0h， 以0.35 g的产率得到3,7,7-trimethylbicyclo<4.1.0>hept-2-en-4-one oxime
  参考文献：
  名称：

  Tkachev, A. V.; Rukavishnikov, A. V.; Korobeinicheva, T. O., Journal of Organic Chemistry USSR (English Translation), 1990, vol. 26, # 9.2, p. 1676 - 1682

  摘要：

  DOI：

文献信息

• Syntheses and crystal structure of bridged Os3-clusters with chiral 3-carane-type ligands
  作者：Vladimir A. Maksakov、Vladimir P. Kirin、Pavel A. Petukhov、Tatjana V. Rybalova、Yuri V. Gatilov、Alexey V. Tkachev

  DOI：10.1016/s0022-328x(00)00153-4

  日期：2000.6

  Reaction of (μ-H)2Os3(CO)10 cluster with (1S,3S,6R)-3-dimethylaminocarane-4-one E-oxime results in loss of dimethylamino group and formation of (μ-H)Os3(CO)10(μ-ONC) cluster (43%). Treatment of cluster Os3(CO)11(NCCH3) with (1S,3S,6R)-3-mercaptocaran-4-one E-oxime gives cluster (μ-H)Os3(CO)10(μ-S⋯) in 86%, whose structure was proved by X-ray single crystal analysis. Decarbonylation of the later

  （μ-H）2 Os 3（CO）10团簇与（1 S，3 S，6 R）-3-二甲基氨基戊烷-4-one E-肟的反应导致二甲基氨基基团的丢失和（μ-H Os 3（CO）10（μ-ONC）簇（43％）。簇的治疗锇3（CO）11（NCCH 3）与（1小号，3小号，6 - [R）-3- mercaptocaran -4-酮ë肟给出簇（μ-H）O的3（CO）10（μ-S⋯）为86％，其结构通过X射线单晶分析证明。与后来的化合物脱羰（CH 3）3 NO导致（μ-H）O的非对映体混合物3（CO）9（μ，η 2 - （小号，Ñ）⋯）以64％的产率簇。
• ——
  作者：P. A. Petukhov、S. N. Bizyaev、À. V. Tkachev

  DOI：10.1023/a:1015097200993

  日期：——

  The reaction of nitroso chlorides of natural monoterpene hydrocarbons, 3-carene and alpha-pinene, with simple alpha,omega-diamines (1,2-diaminoethane, 1,3-diaminopropane, piperazine, 1,6-diaminohexane, diethylenetriamine) results in the formation of alpha-amino oximes and bis-alpha-amino oximes. The product structures were proved by spectroscopy. The procedures of separation and purification of diamino oximes and diamino dioximes are described. Detailed analysis of the H-1 and C-13 NMR spectra of the new chiral nitrogen-containing derivatives was carried out.