(+/-)-3-methylene-1,5-diphenylpentanediol | 71370-00-8

• 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-1,5-diphenylpentanediol
• 英文别名: 1,5-Diphenyl-3-methylenepentane-1,5-diol；3-Methylene-1,5-diphenylpentan-1,5-diol；3-Methylidene-1,5-diphenylpentane-1,5-diol
• CAS: 71370-00-8
• 化学式: C₁₈H₂₀O₂
• 分子量: 268.356
• InChiKey: MMHDHCWCJQIFGK-UHFFFAOYSA-N

物化性质

• 沸点：
  452.0±40.0 °C(Predicted)
• 密度：
  1.116±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-氯-2-氯甲基丙烯 以18%的产率得到
  参考文献：
  名称：

  Chao-Jun Li, Tetrahedron Lett, 36 (1995) N 4, S 517-518

  摘要：

  DOI：

文献信息

• A Mild and Convenient Barbier-Type Allylation of Aldehydes to Homoallylic Alcohols via Iodide Ion Promoted Stannylation of Allylic Bromides and Chlorides with Tin(II) Chloride
  作者：Toshiro Imai、Shinya Nishida

  DOI：10.1055/s-1993-25871

  日期：——

  Barbier-type allylation of aldehydes with allylic bromides and tin(II) chloride dihydrate is largely accelerated by adding stoichiometric or substoichiometric amounts of sodium iodide. This method has some merits such as lower temperature, shorter reaction time and/or more choices of solvents for the reaction. Moreover, the activation by the iodide ion enables the use of relatively unreactive allylic chlorides of various structural types (e.g., 3-chloro-2-chloromethylpropene as an isobutene dianion equivalent) and, thus, expands synthetic applicability of this reaction. The major role of the iodide salt is attributed to the in situ generation of the corresponding allylic iodide.

  巴比尔型醛与烯丙基溴和二水合氯化亚锡的偶联反应通过添加化学计量或亚化学计量的碘化钠，得到了显著的加速。这种方法具有一些优点，如较低的反应温度、更短的反应时间以及/或更多选择性的溶剂使用。此外，碘离子引发的活化使得可以利用相对不活泼的各种结构类型的烯丙基氯化物（例如，作为异丁烯二负离子等价物的3-氯-2-氯甲基丙烯），从而扩大了这一反应的合成应用范围。碘盐的主要作用归因于其在位生成相应的烯丙基碘化物。
• 3-Methylseleno-2-[methylselenomethyl]-propene valuable precursor of trimethylenemethane and trimethylenemethane dianion
  作者：Alain Krief、Willy Dumont

  DOI：10.1016/s0040-4039(96)02385-4

  日期：1997.1

  3-Methylseleno-2-[methylselenomethyl]-propene proved to be a valuable precursor of 3-lithio-2-[methylselenomethyl]-propene and 3-lithio-2-[lithiomethyl]-propene. These have been reacted with various electrophiles and have in turn be successfully transformed into functionalized cyclic ethers.

  3-甲基硒基-2- [甲基硒基甲基]-丙烯被证明是3-硫基-2- [甲基硒基甲基]-丙烯和3-硫基-2- [硫代甲基]-丙烯的有价值的前体。这些已与各种亲电试剂反应，并已成功地转化为官能化的环醚。
• Generation of allyl- and benzyllithiums from the corresponding halides by the aid of lithium-tellurium exchange reactions
  作者：Takahiro Kanda、Shinzi Kato、Takushi Sugino、Nobuaki Kambe、Noboru Sonoda

  DOI：10.1016/0022-328x(94)80107-x

  日期：1994.6

  products under similar conditions arising from the competing lithium-halogen exchange and/or the displacement of the halogen atom with organolithiums used, but they were converted selectively to benzyllithiums in ether without affecting halogen substituents on the benzene ring. Several allyllithiums including dilithioisobutene were generated from allylic halides in a similar way via allylic tellurides

  通过从相应卤化物原位生成的烯丙基和苄基碲化物的锂-碲交换反应，可以制备各种烯丙基和苄基锂。生成的有机锂已成功被亲电子试剂（如醛，酮和三甲基氯硅烷）捕获。在THF中有效地生成在其芳族环上具有烷基，烷氧基，氟，氯或氰基取代基的苄基锂。带有溴或碘取代基的苄基碲化物在相似条件下由于竞争性的锂-卤素交换和/或使用有机锂置换卤素原子而提供了产物混合物，但在不影响卤素取代基的情况下，它们在醚中选择性地转化为苄基锂。在苯环上。经由烯丙基碲化物以类似方式由烯丙基卤化物产生包括二硫代异丁烯在内的几种烯丙基锂。在检查的任何反应中，Wurtz型偶联都可以忽略不计。
• Palladium-catalysed carbonyl allylation by 2-methylenepropane-1,3-diol
  作者：Yoshiro Masuyama、Masaaki Kagawa、Yasuhiko Kurusu

  DOI：10.1039/cc9960001585

  日期：——

  2-Methylenepropane-1,3-diol first allylates an aldehyde exclusively at the allylic alcohol moiety at room temperature and then, at 50 °C, allylates another aldehyde also at the allylic alcohol moiety, in the presence of a catalytic amount of PdCl2(PhCN)2 with tin(II) chloride.

  2-甲烯基丙烷-1,3-二醇首先在室温下选择性地在烯丙醇部分对醛进行烯丙基化，然后在50°C下，在催化量的PdCl2(PhCN)2和氯化亚锡的存在下，再次在烯丙醇部分对另一个醛进行烯丙基化。
• Naphthalene-catalysed lithiation of 3-chloro-2-chloromethyl-propene: A barbier-type practical alternative to the trimethylenemethane dianion
  作者：Diego J. Ramón、Miguel Yus

  DOI：10.1016/0040-4039(92)88181-4

  日期：1992.4

  The reaction of equimolar amounts of 3-chloro-2-chloromethylpropene (2) and a carbonyl compound (3) with an excess of lithium powder and a catalytic amount (6%) of naphthalene in tetrahydrofuran at −78°C leads, after hydrolysis with water, to the corresponding diols 4 in a Barbier-type process.

  水解后，等摩尔量的3-氯-2-氯甲基丙烯（2）和羰基化合物（3）与过量的锂粉和催化量的萘（6％）在四氢呋喃中的反应在-78℃下反应与水一起以Barbier型方法得到相应的二醇4。