(Z)-3-methylhexa-3,5-dien-1-ol | 912356-83-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (Z)-3-methylhexa-3,5-dien-1-ol
• 英文别名: (3Z)-3-methylhexa-3,5-dien-1-ol
• CAS: 912356-83-3
• 化学式: C₇H₁₂O
• 分子量: 112.172
• InChiKey: JQLHPZVSICDDQT-DAXSKMNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-3-methylhexa-3,5-dien-1-ol 在 吡啶 、 N-碘代丁二酰亚胺 、 盐酸羟胺 、 戴斯-马丁氧化剂 、 臭氧 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 24.3h， 生成 (5-methyl-3-phenyl-4,5-dihydroisoxazol-5-yl)methanol
  参考文献：
  名称：

  Catalytic Enantioselective 1,4-Iodofunctionalizations of Conjugated Dienes

  摘要：

  The first catalytic enantioselective 1,4-iodofunctionalizations of conjugated dienes have been developed. Starting from beta,gamma,delta,epsilon-unsaturated oximes and 4-Ns hydrazones, these N-iodosuccinimide-mediated reactions are catalyzed by newly modified tertiary aminothiourea derivatives and furnish Delta(2)-isoxazoline and Delta(2)-pyrazoline derivatives, respectively, containing an (E)-allyl iodide group at the quaternary stereogenic center generally in high yield and with excellent enantioselectivity (up to 98.5:1.5 er).

  DOI：

  10.1021/acs.orglett.5b02026
• 作为产物：
  描述：

  4-甲基-5,6-二氢吡喃-2-酮 在 potassium tert-butylate 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 、 环己烷 为溶剂， 反应 3.5h， 生成 (Z)-3-methylhexa-3,5-dien-1-ol
  参考文献：
  名称：

  Catalytic Enantioselective 1,4-Iodofunctionalizations of Conjugated Dienes

  摘要：

  The first catalytic enantioselective 1,4-iodofunctionalizations of conjugated dienes have been developed. Starting from beta,gamma,delta,epsilon-unsaturated oximes and 4-Ns hydrazones, these N-iodosuccinimide-mediated reactions are catalyzed by newly modified tertiary aminothiourea derivatives and furnish Delta(2)-isoxazoline and Delta(2)-pyrazoline derivatives, respectively, containing an (E)-allyl iodide group at the quaternary stereogenic center generally in high yield and with excellent enantioselectivity (up to 98.5:1.5 er).

  DOI：

  10.1021/acs.orglett.5b02026

文献信息

• Synthetic Study of 1,3-Butadiene-Based IMDA Approach to Construct a [5−7−6] Tricyclic Core and Its Application to the Total Synthesis of C8-<i>e</i><i>pi</i>-Guanacastepene O
  作者：Chuang-Chuang Li、Cui-Hua Wang、Bo Liang、Xin-Hao Zhang、Lu-Jiang Deng、Shuang Liang、Jia-Hua Chen、Yun-Dong Wu、Zhen Yang

  DOI：10.1021/jo060996h

  日期：2006.9.1

  An efficient intramolecular Diels-Alder (IMDA) strategy for the construction of the [5-7-6] tricyclic core (18) of guanacastepenes has been developed from cis-and trans-1,3-butadiene-tethered-4-oxopent-2- ynoic acid ethyl esters 10 and 11. This method facilitates the synthesis of C8-epi-guanacastepene O (36) in a very efficient manner.