2-Benzyliden-4-methylcyclohexanon | 75910-68-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-Benzyliden-4-methylcyclohexanon
• 英文别名: (+/-)-1-methyl-3-(benzylidene-(seqtrans))-cyclohexanone-(4)；(+/-)-1-Methyl-3-(benzyliden-(seqtrans))-cyclohexanon-(4)；2-Benzylidene-4-methylcyclohexanone；(2E)-2-benzylidene-4-methylcyclohexan-1-one
• CAS: 75910-68-8
• 化学式: C₁₄H₁₆O
• 分子量: 200.28
• InChiKey: ZQGNKNYBPLSFHO-JLHYYAGUSA-N

物化性质

• 沸点：
  335.7±22.0 °C(Predicted)
• 密度：
  1.050±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  2-Benzyliden-4-methylcyclohexanon 在 PPA 作用下， 生成 苄基甲苯
  参考文献：
  名称：

  Conia,J.-M.; Amice,P., Bulletin de la Societe Chimique de France, 1970, p. 2972 - 2980

  摘要：

  DOI：
• 作为产物：
  描述：

  4-甲基环己酮 、 苯甲醛 生成 2-Benzyliden-4-methylcyclohexanon
  参考文献：
  名称：

  OLSEN, ROBERT J.;MINNIEAR, JOHN C.;OVERTON, W. MACK;SHERRICK, JOHN M., J. ORG. CHEM., 56,(1991) N, C. 989-991

  摘要：

  DOI：

文献信息

• Pd(II)-Catalyzed Synthesis of Alicyclic[<i>b</i>]-Fused Pyridines via C(sp²)–H Activation of <i>α,β</i>-Unsaturated <i>N</i>-Acetyl Hydrazones with Vinyl Azides
  作者：Biao Nie、Wanqing Wu、Chuanfei Jin、Qingyun Ren、Ji Zhang、Yingjun Zhang、Huanfeng Jiang

  DOI：10.1021/acs.joc.1c02086

  日期：2022.1.7

  A new synthetic protocol for alicyclic[b]-fused pyridines with complete regioselectivity from α,β-unsaturated N-acetyl hydrazones and vinyl azides via Pd(II)-catalyzed C–H activation/cyclization/aromatization strategy has been described. A series of five- to eight-membered alicyclic[b]-fused pyridines were prepared in a one-step manner with wide substrate scope and good functional group tolerance.

  已经描述了一种通过 Pd(II) 催化的 C-H 活化/环化/芳构化策略从α,β-不饱和N-乙酰腙和乙烯基叠氮化物具有完全区域选择性的脂环族[ b ]-稠合吡啶的新合成方案。一步法制备了一系列具有广泛底物范围和良好官能团耐受性的五至八元脂环[ b ]-稠合吡啶。
• Electrophile-Induced Cyclization/Migration Reaction for the Synthesis of 2,3-Dihydro-5-iodopyran-4-one
  作者：Shu-Guang Wen、Wei-Min Liu、Yong-Min Liang

  DOI：10.1021/jo800556e

  日期：2008.6.1

  A novel method for the construction of 2,3-dihydro-5-iodopyran-4-one through a domino cyclization/migration reaction of 1-alkynyl-2,3-epoxy alcohol was developed. Wet solvent is essential for this reaction. The resulting iodine-containing product can be readily elaborated to more complex products by using known organopalladium chemistry.

  提出了一种通过1-炔基-2,3-环氧醇的多米诺环化/迁移反应构建2,3-二氢-5-碘吡喃-4-酮的新方法。湿溶剂对于该反应是必不可少的。通过使用已知的有机钯化学，可以容易地将所得的含碘产物精加工成更复杂的产物。
• Brønsted Acid Catalyzed Cyclization of Hydroxylated Enynes: A Concise Synthesis of Five-Membered Heterocycles
  作者：Ke-Gong Ji、Jin Chen、Hai-Tao Zhu、Fang Yang、Ali Shaukat、Yong-Min Liang

  DOI：10.1002/chem.201002222

  日期：2011.1.3

  heterocyclic compounds from hydroxylated enynes has been developed. In this reaction, hydroxylated enynes were selectively transformed into five‐membered heterocyclic compounds 2, with an allene moiety at the 3‐position, in the presence of F3CSO3H (0.1 mol %). When R1, R2=Ph, diphenylvinyl‐2,3‐dihydro‐1H‐pyrrole (2 y) was obtained. With HSbF6 (5 mol %) as the catalyst, polycyclic skeletons 3 and 4 with adjacent

  已经开发了从羟基化的炔烃形成五元杂环化合物的温和而直接的途径。在该反应中，在F 3 CSO 3 H（0.1 mol％）存在的情况下，将羟基化的炔烃选择性地转化为五元杂环化合物2，其烯丙基位于3位。当R 1，R 2 = Ph时，得到二苯基乙烯基-2,3-二氢-1 H-吡咯（2 y）。用HSbF 6（5mol％）作为催化剂，获得具有相邻立构中心的多环骨架3和4。当R 1 = H和R 2时=形成了苯乙烯，1,3-二烯基-2,5-二氢-1 H-吡咯（6 as）。布朗斯台德酸催化的多米诺骨牌工艺涉及形成烯丙基碳阳离子中间体，该中间体很容易被烯烃捕获，从而得到各种新颖的五元杂环骨架。
• Poggi; Saltini, Gazzetta Chimica Italiana, 1932, vol. 62, p. 678,681
  作者：Poggi、Saltini

  DOI：——

  日期：——
• A photoannulation route to naphthalenes from cyclic ketones
  作者：Robert J. Olsen、John C. Minniear、W. Mack Overton、John M. Sherrick

  DOI：10.1021/jo00003a018

  日期：1991.2

  A three-step naphthalene annulation of cyclic ketones has been developed. Aldol condensation with an aromatic aldehyde followed by Wittig olefination produces a 1,3-diene, which undergoes oxidative photocyclization to produce a naphthalene derivative. Ketone ring sizes of C5 to C8 were annulated successfully. The sequence was also applied successfully to three methyl-substituted derivatives and one polycyclic case.