1,3-二羟基十一烷 | 6071-32-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 1,3-二羟基十一烷
• 英文名称: 1,3-undecanediol
• 英文别名: undecane-1,3-diol；Undecan-1,3-diol；n-Undecandiol-1,3；Undecandiol-1,3
• CAS: 6071-32-5
• 化学式: C₁₁H₂₄O₂
• 分子量: 188.31
• InChiKey: CSFUNXXUTSRHPN-UHFFFAOYSA-N

物化性质

• 熔点：
  52°C (estimate)
• 沸点：
  271.93°C (rough estimate)
• 密度：
  0.9314 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3-二羟基十一烷 在 三氟甲磺酸三甲基硅酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 (4R,6S,8R,11S)-8-methyl-4-octyl-11-propan-2-yl-1,5-dioxaspiro[5.5]undecane
  参考文献：
  名称：

  Stereoselective acetalization of 1,3-alkanediols by l-menthone: application to the resolution of racemic 1,3-alkanediols and to the determination of the absolute configuration of enantiomeric 1,3-alkanediols

  摘要：

  A general and reliable method for the resolution of racemic 1,3-alkanediols, which involves their conversion into diastereomeric spiroacetals derived from l-menthone, is described. Thus, the reaction of the bis-O-trimethylsilyl derivatives of racemic 1,3-alkanediols with l-menthone in the presence of a catalytic amount of trimethylsilyl trifluoromethanesulfonate affords the diastereomeric spiroacetals 3 and 4. The two can be readily separated by silica gel column chromatography. Hydrolysis of each diastereomer under acidic conditions liberates the corresponding enantiomerically pure diol. An empirically derived correlation of configuration and H-1 NMR chemical shifts for spiroacetals 3 and 4 has been developed which is rationalized based on long-range effects due to the magnetic anisotropy inherent to the menthane ring in a rigid spiroacetal conformation. The method described here should be widely applicable to the determination of the absolute configuration of various 1,3-alkanediols.

  DOI：

  10.1021/jo00031a019
• 作为产物：
  描述：

  1-十一烯 在 叔丁基过氧化氢 、 selenium(IV) oxide 、 二甲基硫 、 双氧水 、 sodium acetate 、 diborane(6) 作用下， 反应 38.0h， 生成 1,3-二羟基十一烷
  参考文献：
  名称：

  Rao, A. V. Rama; Mysorekar, Sudha V.; Yadav, J. S., Synthetic Communications, 1987, vol. 17, # 11, p. 1339 - 1348

  摘要：

  DOI：

文献信息

• Cerium or Ruthenium Catalyzed Oxidation of Alcohols to Carbonyl Compounds by Means of Sodium Bromate
  作者：Shigekazu Kanemoto、Hiroki Tomioka、Koichiro Oshima、Hitosi Nozaki

  DOI：10.1246/bcsj.59.105

  日期：1986.1

  alcohols in the presence of cerium or ruthenium compounds in biphase reaction. Selective oxidation of secondary alcohols was performed in the presence of primary ones using cerium(IV) ammonium nitrate (CAN) or cerium(IV) sulfate (CS) as catalyst. For instance, treatment of 1,10-undecanediol with CS/NaBrO3 provided 11-hydroxy-2-undecanone in 82% yield. Ruthenium catalyzed biphase oxidation of alcohols

  已发现溴酸钠是在双相反应中在铈或钌化合物存在下氧化醇的有效氧化剂。仲醇的选择性氧化在伯醇存在下使用硝酸铈 (IV) 铵 (CAN) 或硫酸铈 (IV) (CS) 作为催化剂进行。例如，用 CS/NaBrO3 处理 1,10-十一烷二醇以 82% 的产率提供 11-羟基-2-十一烷酮。钌催化醇与溴酸钠的双相氧化以良好至极好的产率提供相应的醛或酮。
• Natural acetylenes. Part XVIII. Some allenic polyacetylenes from basidiomycetes
  作者：R. E. Bew、J. R. Chapman、Ewart R. H. Jones、B. E. Lowe、G. Lowe

  DOI：10.1039/j39660000129

  日期：——

  The isolation, characterisation, and structure determination of ten polyacetylenes, including seven new allenic-diactylenes, from five Basidiomycete fungi (Cortinellus berkeleyanus, Odontia bicolor, Flammula sapinea, Daedalea juniperina, and the unidentified fungus B285) are described. The new allenic-diacetylenes are (a) HCC·CC·CHCCH·[CH2]n·OH (n= 1, 3, and 4); (b) HCC·CC·CHCCH·CH(OH)·[CH2]n·OH (n=

  描述了十种聚乙炔的分离，表征和结构测定，其中包括五种担子菌（Cortinellus berkeleyanus，Odontia bicolor，Flamula sapinea，Daedalea juniperina和未鉴定的真菌B285）中的十种聚乙炔，其中包括七种新的烯丙基二乙炔。新的烯丙基二乙炔为（a）HC C·C C·CH C CH·[CH 2 ] n ·OH（n = 1、3和4）；（b）HC C·C C·CH C CH·CH（OH）·[CH 2 ] n ·OH（n = 2和3）；（c）HC C·C C·CH C CH·CH 2 ·CH（OH）·CH 2 ·CH2 ·OH；（d）CH 3 ·CC·CC·CHCCH·CH 2 ·CH 2 ·OH。方便地纯化二醇（b； n = 2）和（c），并检查它们的异亚丙基衍生物。
• Silafunctional compounds in organic synthesis. 30. Intramolecular hydrosilation of alkenyl alcohols: A new approach to the regioselective synthesis of 1,2- and 1,3-diols
  作者：Kohei Tamao、Tetsu Tanaka、Takashi Nakajima、Ritsuo Sumiya、Hitoshi Arai、Yoshihiko Ito

  DOI：10.1016/s0040-4039(00)84800-5

  日期：1986.1

  Intramolecular hydrosilation of allyl and homoallyl alcohols and the subsequent oxidative cleavage of the resultant carbon—silicon bond have provided a new approach to the regio-controlled synthesis of 1,2- and/or 1,3-diols.

  烯丙基和高烯丙基醇的分子内硅氢化作用以及随后的碳-硅键氧化裂解为区域控制1，2-和/或1,3-二醇的合成提供了一种新方法。
• An enantiodifferentiating conversion of racemic 1,3-alkanediols into enantiomerically pure materials
  作者：Toshiro Harada、Hideaki Kurokawa、Akira Oku

  DOI：10.1016/s0040-4039(00)96641-3

  日期：1987.1

  Titanium tetrachloride promoted ring-cleavage reaction of a mixture of diastereomeric spiroketals derived from racemic 1,3-alkanediols and ℓ-menthone, followed by benzoylation by Mitsunobu reaction, and the subsequent hydrolysis gave enantiomerically pure 1,3-alkanediols.

  四氯化钛促进了由外消旋1，3-链烷二醇和β-薄荷酮衍生的非对映异构螺环混合物的开环反应，随后通过Mitsunobu反应进行苯甲酰化，随后水解得到对映体纯的1,3-链烷二醇。
• 1,3-FATTY DIOL COMPOUNDS AND DERIVATIVES THEREOF
  申请人：REG Life Sciences LLC

  公开号：US20180072645A1

  公开（公告）日：2018-03-15

  The disclosure relates to the field of specialty chemicals. In particular, the disclosure provides novel 1,3-fatty-diol compounds and derivatives thereof which are useful e.g., in the production of personal care products, surfactants, detergents, polymers, paints, coatings, and as emulsifiers, emollients, and thickeners in cosmetics and foods, as industrial solvents and plasticizers, etc.

  本公开涉及专业化学领域。具体而言，本公开提供了新颖的1,3-脂肪二醇化合物及其衍生物，可用于个人护理产品、表面活性剂、洗涤剂、聚合物、涂料、涂层的生产，以及作为化妆品和食品中的乳化剂、润肤剂和增稠剂，工业溶剂和增塑剂等。