(S)-1-undecen-5-ol

• 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: (S)-1-undecen-5-ol
• 英文别名: (5S)-undec-1-en-5-ol
• 化学式: C₁₁H₂₂O
• 分子量: 170.295
• InChiKey: AABJJOUBFQRBLD-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 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：

  (S)-1-undecen-5-ol 在 4-二甲氨基吡啶 、 Schwartz's reagent 、 双(三甲基硅烷基)氨基钾 、 sodium hydride 、 臭氧 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 异丙醇 、 mineral oil 为溶剂， 反应 31.08h， 生成 (2S,6S)-6-hexyltetrahydro-2H-pyran-2-carbaldehyde
  参考文献：
  名称：

  （+）-Chamuvarinin，一种有效的抗癌药和抗锥虫病药，无立体选择性保护的不对称总合成：通过内部烷基化的邻位连接的氧三环核的底物控制结构

  摘要：

  已经完成了一种有效的抗癌和抗胰凝乳剂（+）-香豆素（1）的无立体选择性保护的不对称全合成。该天然产物具有七个立体定位中心的相邻连接的[双（四氢呋喃）]四氢吡喃（THF-THF-THP）核是以完全受底物控制的方式构建的。氧杂三环核心的环间立体化学（threo，threo，threo）是通过螯合控制的Keck烯丙基化以立体选择性方式建立的，而环内顺式或反式相对立体化学则是通过立体选择性内部烷基化来控制的。

  DOI：

  10.1021/acs.orglett.8b02706
• 作为产物：
  描述：

  1,2-环氧辛烷 在 copper(l) iodide 、 (S,S)-(+)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(II) 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 24.25h， 生成 (S)-1-undecen-5-ol
  参考文献：
  名称：

  Iron(III) Catalyzed Direct Synthesis of cis-2,7-Disubstituted Oxepanes. The Shortest Total Synthesis of (+)-Isolaurepan

  摘要：

  Prins cyclization of bis-homoallylic alcohols with aldehydes catalyzed by iron(III) salts shows excellent cis selectivity and yields to form 2,7-disubstituted oxepanes. The iron(III) is able to catalyze this process with unactivated olefins. This cyclization was used as the key step in the shortest total synthesis of (+)-isolaurepan.

  DOI：

  10.1021/ol3028016

文献信息

• Ti-TADDOLate-catalyzed, highly enantioselective addition of alkyl- and aryl-titanum derivatives to aldehydes
  作者：Beat Weber、Dieter Seebach

  DOI：10.1016/s0040-4020(01)90475-2

  日期：——

  Toluene-ether or toluene-hexane solutions of aryl and alkyl triisopropoxy titanium reagents (free of Li, Mg, or Zn salts) are prepared from the corresponding Li or Grignard reagents and ClTi((OPr)-Pr-i)(3), with careful removal of salts (centrifugation of LiCl or of dioxane.MgX(2), and addition of 12-crown-4). The solutions of the organotitanium compounds are combined with one equiv. of an aldehyde and 0.2 equiv. of (R,R)-diisopropoxy-(alpha,alpha,alpha',alpha'-tetraphenyl-2,2-dimethyl-1,3-dioxolane-4,5-dimethanolato) titanium (Ti-TADDOLate 3) at dry-ice temperature. Warming up to room temperature leads to nucleophilic addition to the (Si)-face of the aldehydes with enantioselectivities as high as 99.5 : 0.5 (products 4 - 33 in Scheme 4). Functional groups or protecting groups and branching in the Ti-R group and in the aldehyde must be remote from the reacting centers. Aryl groups can be added to aldehydes by this method. - In contrast to all the enantioselective R(2)Zn additions to aldehydes, in which only one R-group is actually transferred, a twice as economic use is made of the originally employed R-metal reagent in the method described here. - A procedure for multigram preparation of the spiro-Ti-TADDOLate (2) employed for the in situ generation of the catalyst (3) is described, and details of the determination of enantiomer ratios (er) by GC and NMR methods are given (Tab. 2, 3). The mechanistic interpretation of Ti-TADDOLate-mediated nucleophilic additions as derived previously (ref.(4e)) is also compatible with this monometallic variant of the method.
• Iron(III) Catalyzed Direct Synthesis of <i>cis</i>-2,7-Disubstituted Oxepanes. The Shortest Total Synthesis of (+)-Isolaurepan
  作者：Martín A. Purino、Miguel A. Ramírez、Antonio H. Daranas、Víctor S. Martín、Juan I. Padrón

  DOI：10.1021/ol3028016

  日期：2012.12.7

  Prins cyclization of bis-homoallylic alcohols with aldehydes catalyzed by iron(III) salts shows excellent cis selectivity and yields to form 2,7-disubstituted oxepanes. The iron(III) is able to catalyze this process with unactivated olefins. This cyclization was used as the key step in the shortest total synthesis of (+)-isolaurepan.
• Stereoselective Protection-Free Asymmetric Total Synthesis of (+)-Chamuvarinin, a Potent Anticancer and Antitrypanosomal Agent: Substrate-Controlled Construction of the Adjacently Linked Oxatricyclic Core by Internal Alkylation
  作者：Mallesham Samala、Thien Nhan Lu、Suresh Mandava、Jungjoong Hwang、Ganganna Bogonda、Donghoon Kim、Haeil Park、Deukjoon Kim、Jongkook Lee

  DOI：10.1021/acs.orglett.8b02706

  日期：2018.10.19

  A stereoselective protection-free asymmetric total synthesis of (+)-chamuvarinin (1), a potent anticancer and antitrypanosomal agent, has been accomplished. The adjacently linked [bis(tetrahydrofuran)]tetrahydropyran (THF–THF–THP) core of this natural product with seven stereogenic centers was constructed in a completely substrate-controlled fashion. The inter-ring stereochemistry (threo,threo,threo)

  已经完成了一种有效的抗癌和抗胰凝乳剂（+）-香豆素（1）的无立体选择性保护的不对称全合成。该天然产物具有七个立体定位中心的相邻连接的[双（四氢呋喃）]四氢吡喃（THF-THF-THP）核是以完全受底物控制的方式构建的。氧杂三环核心的环间立体化学（threo，threo，threo）是通过螯合控制的Keck烯丙基化以立体选择性方式建立的，而环内顺式或反式相对立体化学则是通过立体选择性内部烷基化来控制的。