3-methylene-dec-1-en-4-ol | 100281-10-5

• 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: 3-methylene-dec-1-en-4-ol
• 英文别名: 3-methylene-1-decen-4-ol；3-Methylidenedec-1-en-4-ol
• CAS: 100281-10-5
• 化学式: C₁₁H₂₀O
• 分子量: 168.279
• InChiKey: XUCCBXXGOXGJAT-UHFFFAOYSA-N

物化性质

• 沸点：
  243.6±9.0 °C(Predicted)
• 密度：
  0.849±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  3-methylene-dec-1-en-4-ol 生成 3-methylidenedec-1-en-4-yl 4-nitrobenzoate
  参考文献：
  名称：

  WADA, EIJI;KANEMASA, SHUJI;FUJIWARA, ISAMU;TSUGE, OTOHIKO, BULL. CHEM. SOC. JAP., 1985, 58, N 7, 1942-1945

  摘要：

  DOI：
• 作为产物：
  描述：

  庚醛 、 2-氯-1.3-丁二烯 在 LiDBB 作用下， 生成 3-methylene-dec-1-en-4-ol
  参考文献：
  名称：

  手性2-取代-1,3-二烯的Diels-Alder反应中的非对面选择性。

  摘要：

  从氯丁二烯开始，描述了烷基和芳基（1，3-丁二烯-2-基）甲醇1的改进的合成。这些二烯醇或它们的醚3与各种亲二烯体之间的热Diels-Alder反应产生了对单环“对”加合物的公平至良好的区域和非对映选择性。相反，当在路易斯酸的存在下进行二烯醚3的狄尔斯-阿尔德环加成反应时，观察到总区域选择性和优异的π表面选择性。

  DOI：

  10.1016/s0040-4039(00)60028-x

文献信息

• Stannyldienes, new tools for organic synthesis. preparatiom and reactivity
  作者：Cristina Nativi、Maurizio Taddei、André Mann

  DOI：10.1016/0040-4020(89)80022-5

  日期：1989.1

  for a regiocontrolled transfer of the dienic structure by : a)tin-lithium exchange and further reaction with aldehydes to give conjugated dienic alcohols; b)coupling with acyl chlorides in the presence of palladium catalysts to give conjugated dienic ketones; c) AlCl3, promoted reaction with acyl chlorides to give allenic ketones.

  三丁基锡烷基-1,3-二烯可以被认为是共轭二烯阴离子的合成等价物。据报道从炔丙基三甲基戊烷开始制备不同取代的2-和3-三烷基锡烷基-1，3-二烯。可以通过（三甲基甲硅烷基）炔丙基醇的加氢甲锡烷基化或（三甲基甲硅烷基）炔丙基酮的甲锡醇杯化来控制二苯乙烯骨架上的苯乙烯基部分的位置。将如此获得的苯乙烯亚胺进行二烯Alder反应，并通过C-Sn将相应的环加合物官能化。键。甲炔还适合通过以下方法进行二烯结构的区域控制转移：a）锡-锂交换，并与醛进一步反应，生成共轭二烯醇；b）在钯催化剂的存在下与酰氯偶联，得到共轭二烯酮；c）AlCl 3，促进与酰氯的反应，生成烯丙基酮。
• A Convenient Route to 2-Lithio-1,3-butadiene from Chloroprene<i>via</i>2-Stannyl-1,3-butadiene
  作者：Eiji Wada、Shuji Kanemasa、Isamu Fujiwara、Otohiko Tsuge

  DOI：10.1246/bcsj.58.1942

  日期：1985.7

  A convenient route to 2-lithio-1,3-butadiene from chloroprene via a 2-stannyl-1,3-butadiene is presented, and the regioselecdve additions to a variety of carbonyl groups are demonstrated.

  提出了通过 2-甲锡烷基-1,3-丁二烯从氯丁二烯制备 2-锂硫-1,3-丁二烯的便捷途径，并证明了区域选择性加成到各种羰基。
• Diastereofacial selectivity in Diels-Alder reactions of chiral 2-substituted-1,3-dienes.
  作者：Robert Bloch、Nathalie Chaptal-Gradoz

  DOI：10.1016/s0040-4039(00)60028-x

  日期：1992.10

  described. Thermal Diels-Alder reactions between these dienols or their ethers 3 and various dienophiles give rise with fair to good regio- and diastereoselectivity to monocyclic “para” adducts. In contrast a total regioselectivity and an excellent π-facial selectivity is observed when the Diels-Alder cycloadditions of the dienic ethers 3 are conducted in the presence of a Lewis acid.

  从氯丁二烯开始，描述了烷基和芳基（1，3-丁二烯-2-基）甲醇1的改进的合成。这些二烯醇或它们的醚3与各种亲二烯体之间的热Diels-Alder反应产生了对单环“对”加合物的公平至良好的区域和非对映选择性。相反，当在路易斯酸的存在下进行二烯醚3的狄尔斯-阿尔德环加成反应时，观察到总区域选择性和优异的π表面选择性。
• Organometallic Reactions in Aqueous Media. Indium-Mediated 1,3-Butadien-2-ylation of Carbonyl Compounds
  作者：Wenshuo Lu、Jihai Ma、Yang、Tak Hang Chan

  DOI：10.1021/ol000239k

  日期：2000.11.1

  Indium-mediated coupling of 1,4-dibromo-2-butyne with carbonyl compounds in aqueous media gave good yields of the 1, 3-butadien-2-ylmethanols.

  在水介质中，铟介导的1，4-二溴-2-丁炔与羰基化合物的偶合得到1，3-丁二烯-2-基甲醇的良好产率。
• Thermal and Catalyzed Diels-Alder Reactions with Chiral 2-Substituted-1,3-dienes: Conformational Models for Diastereofacial Selectivity
  作者：Robert Bloch、Nathalie Chaptal-Gradoz

  DOI：10.1021/jo00094a029

  日期：1994.7

  The thermal or BF3-catalyzed Diels-Alder reactions of chiral 2-substituted-1,3-dienes bearing a hydroxy or a protected hydroxy group at the allylic position with various dienophiles have been studied in order to determine the regio- and stereoselective control elements. Good regio- and facial selectivities were ob;served in thermal reaction of dienes bearing a free hydroxy group. The stereoselectivity was reversed and strongly lowered when the hydroxy soup was protected as an ether. However the regio- as well as the stereoselectivity of the cycloaddition of these diene ethers with alpha,beta-unsaturated aldehydes or ketones are remarkably enhanced by the addition of a Lewis acid since in a few cases a unique isomer was formed. These experimental results have been rationalized and could be explained by conformational preferences of the dienes in the transition state. In particular, the reversal of facial selectivity for dienes having a free hydroxy group has been attributed to a hydrogen bonding interaction between the diene and the dienophile.