(+/-)-undec-10-en-2-ol | 91523-75-0

• 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: (+/-)-undec-10-en-2-ol
• 英文别名: undec-10-en-2-ol；10-undecen-2-ol
• CAS: 91523-75-0
• 化学式: C₁₁H₂₂O
• 分子量: 170.295
• InChiKey: WGIQZNYDKSWERR-UHFFFAOYSA-N

物化性质

• 沸点：
  155 °C(Press: 30 Torr)
• 密度：
  0.838±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  12
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  (+/-)-undec-10-en-2-ol 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 以100%的产率得到2-十一醇
  参考文献：
  名称：

  Arbain, Dayar; Dasman,; Ibrahim, Satria, Australian Journal of Chemistry, 1990, vol. 43, p. 1949 - 1952

  摘要：

  DOI：
• 作为产物：
  描述：

  十一碳-10-烯-2-酮 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 12.0h， 以90%的产率得到(+/-)-undec-10-en-2-ol
  参考文献：
  名称：

  Arbain, Dayar; Dasman,; Ibrahim, Satria, Australian Journal of Chemistry, 1990, vol. 43, p. 1949 - 1952

  摘要：

  DOI：

文献信息

• Terminal alkene monoisomerization catalysts and methods
  申请人：San Diego State University Research Foundation

  公开号：US09708236B2

  公开（公告）日：2017-07-18

  The invention provides novel catalysts and methods of using catalysts for controlling the position of a double bond and cis/trans-selectivity in isomerization of terminal alkenes to their 2-isomers. Catalysts such as (pentamethylcyclopentadienyl)Ru formulas 1 and 3 having a bifunctional phosphine can be used in the methods. A catalyst loading of 1 mol % of formulas 1+3 can be employed for the production of (E)-2-alkenes at 40-70° C.; lower temperatures can be used with higher catalyst loading. Acetonitrile-free catalysts can be used at lower loadings, room temperature, and in less than a day to accomplish the same results as catalysts 1+3. The novel catalyst systems minimize thermodynamic equilibration of alkene isomers, so that the trans-2-alkenes of both non-functionalized and functionalized alkenes can be generated.

  该发明提供了新型催化剂和使用催化剂的方法，用于控制双键的位置以及顺式/反式选择性，在将末端烯烃异构化为它们的2-异构体过程中。这些催化剂，比如（五甲基环戊二烯基）钌配方1和3，具有双功能膦基，可用于这些方法。配方1+3的1摩尔%的催化剂负载可用于在40-70°C下生产（E）-2-烯烃；较高的催化剂负载可以使用更低的温度。无乙腈催化剂可以在较低的负载、室温和不到一天的时间内完成与配方1+3相同的结果。这种新型催化系统最小化了烯烃异构体的热力学平衡，因此可以生成非官能化和官能化烯烃的反式-2-烯烃。
• The Total Synthesis of Both Enantiomers of the Macrocyclic Lactone Zearalane
  作者：Franz Bracher、Jürgen Krauß

  DOI：10.1002/1099-0690(200112)2001:24<4701::aid-ejoc4701>3.0.co;2-6

  日期：2001.12

  A straightforward approach to both enantiomers of zearalane is described from the enantiomerically pure alkenol (S)-4, prepared by a kinetic enzymatic resolution of the racemate. The key step is a Pd-catalyzed cross-coupling of an arene trifluoromethanesulfonate with a 9-alkyl-9-borabicyclo[3.3.1]nonane derivative. The two enantiomers 2a and 2b have been obtained in an enantiodivergent manner by macrolactonization

  从对映体纯烯醇 (S)-4 描述了一种直接的方法来处理玉米赤霉烯的两种对映异构体，该烯醇 (S)-4 通过外消旋体的动力学酶拆分制备。关键步骤是 Pd 催化的芳烃三氟甲磺酸酯与 9-烷基-9-硼双环 [3.3.1] 壬烷衍生物的交叉偶联。两种对映异构体 2a 和 2b 已通过羟基酸 (S)-7 的大环内酯化与 Corey 内酯化的 Gerlach 修饰或 Mitsunobu 内酯化以对映发散方式获得。
• Oxidation of Alcohols with Catalytic Amounts of IBX
  作者：Athanassios Giannis、Agnes Schulze

  DOI：10.1055/s-2005-924764

  日期：——

  we present a catalytic IBX-based method for the oxidation of alcohols. Using this system a variety of benzylic alcohols were transformed to aldehydes in good yields whereas secondary alcohols were easily converted to ketones. Primary aliphatic alcohols were oxidised to the corresponding carboxylic acids. 2-Iodobenzoic acid can also be used instead of IBX.

  在此，我们提出了一种基于催化 IBX 的醇氧化方法。使用该系统，多种苯甲醇以良好的收率转化为醛，而仲醇很容易转化为酮。脂肪族伯醇被氧化成相应的羧酸。也可以使用 2-碘苯甲酸代替 IBX。
• TERMINAL ALKENE MONOISOMERIZATION CATALYSTS AND METHODS
  申请人：San Diego State University Research Foundation

  公开号：US20150231621A1

  公开（公告）日：2015-08-20

  The invention provides novel catalysts and methods of using catalysts for controlling the position of a double bond and cis/trans-selectivity in isomerization of terminal alkenes to their 2-isomers. Catalysts such as (pentamethylcyclopentadienyl)Ru formulas 1 and 3 having a bifunctional phosphine can be used in the methods. A catalyst loading of 1 mol % of formulas 1+3 can be employed for the production of (E)-2-alkenes at 40-70° C.; lower temperatures can be used with higher catalyst loading. Acetonitrile-free catalysts can be used at lower loadings, room temperature, and in less than a day to accomplish the same results as catalysts 1+3. The novel catalyst systems minimize thermodynamic equilibration of alkene isomers, so that the trans-2-alkenes of both non-functionalized and functionalized alkenes can be generated.

  本发明提供了一种新型催化剂及其使用方法，用于控制末端烯烃的异构化反应中双键位置和顺反式选择性的产生。可以使用具有双功能膦基的催化剂，例如（五甲基环戊二烯基）Ru公式1和3。在40-70°C下，可以使用1＋3公式的1摩尔％的催化剂负载来生产（E）-2-烯烃；使用更高的催化剂负载可以使用更低的温度。无乙腈催化剂可以在较低的负载、室温下使用，并在不到一天的时间内完成与1+3催化剂相同的结果。新型催化剂系统最小化烯烃异构体的热力学平衡，从而可以产生非功能化和功能化烯烃的反式-2-烯烃。
• Visible-Light-Promoted Reduction of Epoxides, Hydroxysulfonates, and Halohydrines with Alkyltitanium Alkoxides
  作者：Artyom Mikhaliov、Aliaksei Flerko、Dziyana Atroshchanka、Aliaksei Harakhouski、Arsenii Budko、Kirill Stasko、Andrei Bialkevich、Siarhei Shepialevich、Yahor Rusakovich、Alaksiej Hurski

  DOI：10.1021/acs.orglett.3c03802

  日期：2024.1.12

  Alkyltitanium alkoxides generally serve as nucleophiles in reactions with carbonyl compounds and cross-coupling. Their application as reductants is known but remains underdeveloped. Here, we report that irradiation with visible light makes these organometallic compounds efficient reducing agents for the dehalogenation of 1,2- and 1,3-haloalcohols. This reaction was utilized for the reduction of epoxides

  烷基钛醇盐通常在与羰基化合物的反应和交叉偶联中充当亲核试剂。它们作为还原剂的应用是已知的，但仍未得到开发。在这里，我们报告可见光照射使这些有机金属化合物成为 1,2- 和 1,3- 卤代醇脱卤的有效还原剂。该反应用于环氧化物和磺酸盐的还原，该反应通过一系列原位卤代醇形成和光化学脱卤进行。酯、酰胺、腈、炔和远程溴基团在反应条件下是稳定的。