(3-甲基丁-1,3-二烯-1-亚基)环己烷 | 69719-37-5

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 中文名称: (3-甲基丁-1,3-二烯-1-亚基)环己烷
• 英文名称: (3-Methyl-buta-1,3-dienylidene)-cyclohexane
• CAS: 69719-37-5
• 化学式: C₁₁H₁₆
• 分子量: 148.248
• InChiKey: AOFLVVTWFVGJQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (3-甲基丁-1,3-二烯-1-亚基)环己烷 、 methyl 5-hydroxy-4'-methoxy-7-methyl-4,6'-dioxospiro[4H-1,3-benzodioxine-2,1'-cyclohexa-2',4'-diene]-2'-carboxylate 以 二氯甲烷 、 乙腈 为溶剂， 反应 96.0h， 以23%的产率得到
  参考文献：
  名称：

  Diels–Alder reaction of maldoxin with an isopropenylallene

  摘要：

  The Diels-Alder reaction of maldoxin with an isopropenylallene at 60-75 degrees C afforded an adduct closely related to chloropestolide A (24%) and a second adduct (0-11%) that underwent an ene reaction to generate the chloropupukeanolide D (11-22%) skeleton. The Diels-Alder reaction occurred with good selectively (>5:1) from a single face of maldoxin under much milder conditions than previously reported for the analogous dimethoxycyclohexadienone. Furthermore, the ene reaction took place under mild conditions, whereas the analogous Diels-Alder adduct from the dimethoxycyclohexadienone did not undergo an ene reaction. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.117
• 作为产物：
  描述：

  1-chloro-1-(3-methylbut-3-en-1-ynyl)cyclohexane 以72%的产率得到
  参考文献：
  名称：

  VOSKANYAN M. G.; PASHAYAN A. A.; BADANYAN SH. O., AJKAKAN KIMIAKAN AMSAGIR, ARM. XIM. ZH., 1978, 31, HO 10 750-756

  摘要：

  DOI：

文献信息

• Rhodium(I)‐Catalyzed Three‐Component [4+2+1] Cycloaddition of Two Vinylallenes and CO
  作者：Qi Cui、Zi‐You Tian、Zhi‐Xiang Yu

  DOI：10.1002/chem.202005443

  日期：2021.3.26

  tropone derivatives under mild conditions, where one vinylallene acts as a C4 synthon, the other vinylallene as a C2 synthon, and CO as a C1 synthon. It was proposed that this reaction occurred via oxidative cyclization of the diene part of one vinylallene molecule, followed by insertion of the terminal alkene part of the allene moiety in another vinylallene, into the Rh−C bond of five‐membered rhodacycle

  二烯（或二烯衍生物，如乙烯基丙二烯），炔烃/烯烃和一氧化碳（或碳烯）的过渡金属催化[4 + 2 + 1]反应有望成为合成具有挑战性的七元环化合物的最简单方法，但是到目前为止，仅取得了有限的成功。在此发现，在温和的条件下，两个乙烯基丙二烯和CO之间发生了意外的三组分[4 + 2 + 1]反应，可得到高度官能化的托酮衍生物，其中一个乙烯基丙二烯充当C 4合成子，另一个乙烯基丙二烯充当C 2合成子。和CO作为C 1synthon。有人提出，该反应是通过一个乙烯基丙二烯分子的二烯部分的氧化环化，然后将另一个乙烯基丙二烯中的烯基部分的末端烯烃部分插入五元rhodocycle的Rh-C键中而发生的。然后，CO插入和还原消除得到[4 + 2 + 1]环加合物。此处报道了进一步的实验探索，以了解为何烯/炔-乙烯基烯和CO生成单环托普酮衍生物而不是6 / 7-双环产物。
• Concise Approach to Pupukeanane Skeleton: Synthetic Study of Chloropupukeananin
  作者：Takahiro Suzuki、Susumu Kobayashi

  DOI：10.1021/ol100935w

  日期：2010.7.2

  A concise synthesis of a highly functionalized chloropupukeananin (1) skeleton via a reverse electron-demand Diels-Alder reaction and intramolecular carbonyl-ene reaction sequence based on our proposed biosynthetic pathway is described.
• Controlled Rearrangement of 2,3-Dilithio-1,3-butadienes to 2,5-Dilithio-1,3-butadienes: Synthesis of 2-Isopropylidene-2,5-dihydrosilols
  作者：Adalbert Maercker、H. Wunderlich、Ulrich Girreser

  DOI：10.1002/(sici)1099-0690(199805)1998:5<793::aid-ejoc793>3.0.co;2-3

  日期：1998.5

  3,4-Dilithio-2,5-dimethyl-2,4-hexadiene (4a) rearranges to the cross-conjugated 2,5-dimethylhexadienediyl dianion 11a. A mechanistic investigation proves the intermolecularity of this rearrangement, which is also observed when starting from 4b. The 3-lithio-2,5-dimethylhexadienyl anion Ipa with one vinyllithium and one allyllithium group, is a true intermediate in this rearrangement, its synthetic potential is employed in the reaction with dichlorosilanes to form 2-isopropylidene-2,5-dihydrosilols 8.