23-acetoxy-O-acetyllupanone oxime | 96695-32-8

• 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: 23-acetoxy-O-acetyllupanone oxime
• 英文别名: [(1S,3aR,5aR,5bR,7aR,8S,9E,11aR,11bR,13aR,13bR)-9-acetyloxyimino-3a,5a,5b,8,11a-pentamethyl-1-propan-2-yl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysen-8-yl]methyl acetate
• CAS: 96695-32-8
• 化学式: C₃₄H₅₅NO₄
• 分子量: 541.815
• InChiKey: KZEUQJRHVJENGP-VFVXBFGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.21
• 重原子数：
  39.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  64.96
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  23-acetoxy-O-acetyllupanone oxime 在 sodium tetrahydroborate 、 titanium(III) chloride 、 ammonium acetate 、 sodium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 为溶剂， 反应 92.0h， 生成 24-nor-lupan-3β-ol
  参考文献：
  名称：

  Characterisation of 24-nor-triterpenoids occurring in sediments and crude oils by comparison with synthesized standards

  摘要：

  A series of 24-nor-triterpenoids; 24-nor-urs-12-ene, 24-nor-olean-12-ene and 24-nor-lupane have been identified in sediments and crude oils by comparison with standards obtained by synthesis. A further suite of 24-nor-oleanenes has also been identified by comparison with the acid-catalysed rearrangement products of 24-nor-olean-12-ene. The presence of these components in sedimentary organic matter points to an important new pathway of terrigenous triterpenoid diagenesis.

  DOI：

  10.1016/s0040-4020(01)80903-0
• 作为产物：
  描述：

  乙酸酐 、 lupan-3-one oxime 生成 23-acetoxy-O-acetyllupanone oxime
  参考文献：
  名称：

  Characterisation of 24-nor-triterpenoids occurring in sediments and crude oils by comparison with synthesized standards

  摘要：

  A series of 24-nor-triterpenoids; 24-nor-urs-12-ene, 24-nor-olean-12-ene and 24-nor-lupane have been identified in sediments and crude oils by comparison with standards obtained by synthesis. A further suite of 24-nor-oleanenes has also been identified by comparison with the acid-catalysed rearrangement products of 24-nor-olean-12-ene. The presence of these components in sedimentary organic matter points to an important new pathway of terrigenous triterpenoid diagenesis.

  DOI：

  10.1016/s0040-4020(01)80903-0

文献信息

• Functionalisation of unactivated methyl groups through cyclopalladation reactions
  作者：Jack E. Baldwin、Richard H. Jones、Carmen Najera、Miguel Yus

  DOI：10.1016/s0040-4020(01)96448-8

  日期：1985.1

  through deuteriation or oxidation affords the expected products (21) and (31), or (22), (23), (24), and (32), respectively. The second palladation of the compound (22) takes place on the remaining methyl group yielding the organopalladium derivative (26). Finally, -lupanone oxime is palladated selectively in the 23-position leading to the organopalladium compound (38); the transformation of this compound

  有机钯化合物（3）分别转化为相应的氘代，氯化或氧化衍生物（7），（8）或（9），（11）和（12）。描述。化合物（9）的palpalation发生区域选择性，导致palladated系统（13）转化为双官能化的肟（15）和（16）。的palladation -2,2-二甲基和2,2,6,6-四甲基环己酮肟通向相应的有机钯化合物（17）和（27），其通过deuteriation或氧化，得到预期产物（21）和（ 31）或（22），（23），（24）和（32）。化合物（22）的第二palpalation发生在剩余的甲基上，得到有机钯衍生物（26）。最后，--酮肟在23位上有选择感触，生成有机钯化合物（38）; 还描述了该化合物分别转化为其23-氘和23-乙酰氧基衍生物（41）和（42）的转化。鲁潘酮肟的palladatlon中的立体化学是根据500 MHz下的NOE研究得出的。
• Oxidation of unactivated methyl groups via a cyclopalladation reaction
  作者：Jack E. Baldwin、Carmen Nájera、Miguel Yus

  DOI：10.1039/c39850000126

  日期：——

  The successive cyclopalladation–oxidation of E-pinacolone, E-2,2-dimethylcyclohexanone, 2,2,6,6-tetramethylcyclohexanone, and E-lupanone oxime led to the corresponding β-acetoxy derivatives; the second palladation in the case of the acetoxy compounds (2) and (8) takes place in one of the remaining methyl groups, being a regiospecific process, and in the case of the cyclic oximes the palladation occurs

  E-松果酮，E -2,2-二甲基环己酮，2,2,6,6-四甲基环己酮和E-卢潘酮肟的连续环钯-氧化反应生成相应的β-乙酰氧基衍生物。在乙酰氧基化合物（2）和（8）的情况下，第二palpalation发生在剩余的甲基之一中，这是区域特异性过程，在环状肟的情况下，palpalation发生在赤道甲基中。