α-methylenecamphor | 16161-84-5

• 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: α-methylenecamphor
• 英文别名: 1,7,7-trimethyl-3-methylene-norbornan-2-one；(+/-)-4.7.7-trimethyl-2-methylene-norbornanone-(3)；(+/-)-4.7.7-Trimethyl-2-methylen-norbornanon-(3)；3-Methylen-camphen；(1S,4R)-1,7,7-trimethyl-3-methylidenebicyclo[2.2.1]heptan-2-one
• CAS: 16161-84-5；42931-10-2
• 化学式: C₁₁H₁₆O
• 分子量: 164.247
• InChiKey: XWHIOJOWXZILNH-GZMMTYOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  α-methylenecamphor 、 benzohydroximoyl chloride 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 Bornanon-(2)-(3-spiro-5')-3'-phenyl-Δ^2'-isoxazolin
  参考文献：
  名称：

  Mueller,G., Journal fur praktische Chemie (Leipzig 1954), 1969, vol. 311, p. 118 - 129

  摘要：

  DOI：
• 作为产物：
  描述：

  聚合甲醛 、 左旋樟脑 在 溶剂黄146 、 diethyl amine 作用下， 生成 α-methylenecamphor
  参考文献：
  名称：

  Identification and structure–activity relationship studies of 3-methylene-2-norbornanone as potent anti-proliferative agents presumably working through p53 mediated apoptosis

  摘要：

  We have identified a novel series of alpha-methylene carbonyl compounds through structure-activity relationship (SAR) studies with high levels of anti-proliferative activities. The lead molecule, 3-methylene-2-norbornanone (3) showed potent activity (LC50 = 3-8 muM) against mutant p53 cell types and many fold selectivity (>13-29) over wild-type p53 cells. Further, compound 3 and its analogs showed refolding of mutant p53 protein comparable to their anti-proliferative activities suggesting possible interaction with mutant p53 protein. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.08.048

文献信息

• Exploiting the Facile Release of Trifluoroacetate for the α-Methylenation of the Sterically Hindered Carbonyl Groups on (+)-Sclareolide and (−)-Eburnamonine
  作者：Mark V. Riofski、Jinu P. John、Mary M. Zheng、Julia Kirshner、David A. Colby

  DOI：10.1021/jo102114f

  日期：2011.5.20

  applied this method to produce semisynthetic derivatives of the natural products (+)-sclareolide and (−)-eburnamonine, in which the carbonyl group is proximal to bulky functional groups. Mechanistic insight is also provided from a time course of 19F NMR. Biological evaluation of the natural-product-derived enones led to the identification of a derivative of (−)-eburnamonine with significant cytotoxicity

  报道了一种用于羰基的α-甲基化的有效方法，并且该转化通过在烯烃形成过程中容易地消除三氟乙酸盐来完成。该方法代表了在空间障碍情况下对现有方案的改进，并且我们已经证明了该方法在一系列酮，内酰胺和内酯中的实用性。此外，我们已经应用此方法生产了天然产物（+）-香紫苏内酯和（-）-金枪鱼碱的半合成衍生物，其中羰基基团靠近庞大的官能团。还提供19分钟的时间过程的机械洞察力1 H NMR。对天然产物衍生的烯酮的生物学评估导致鉴定出在耐药MDA-MB-231乳腺癌细胞中具有显着细胞毒性（LC 50 = 14.12μM）的（-）-氨丁胺衍生物。
• Identification and structure–activity relationship studies of 3-methylene-2-norbornanone as potent anti-proliferative agents presumably working through p53 mediated apoptosis
  作者：N. Laxma Reddy、Jeanette Hill、Long Ye、Prabhavathi B. Fernandes、David M. Stout

  DOI：10.1016/j.bmcl.2004.08.048

  日期：2004.11

  We have identified a novel series of alpha-methylene carbonyl compounds through structure-activity relationship (SAR) studies with high levels of anti-proliferative activities. The lead molecule, 3-methylene-2-norbornanone (3) showed potent activity (LC50 = 3-8 muM) against mutant p53 cell types and many fold selectivity (>13-29) over wild-type p53 cells. Further, compound 3 and its analogs showed refolding of mutant p53 protein comparable to their anti-proliferative activities suggesting possible interaction with mutant p53 protein. (C) 2004 Elsevier Ltd. All rights reserved.
• Mueller,G., Journal fur praktische Chemie (Leipzig 1954), 1969, vol. 311, p. 118 - 129
  作者：Mueller,G.

  DOI：——

  日期：——