(+)-undec-1-en-5-ol | 395057-54-2

• 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-1-en-5-ol
• 英文别名: (R)-1-undecen-5-ol；(5R)-undec-1-en-5-ol
• CAS: 395057-54-2
• 化学式: C₁₁H₂₂O
• 分子量: 170.295
• InChiKey: AABJJOUBFQRBLD-NSHDSACASA-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：

  1,2-Benzoldicarbonsaeuremonopent-4-enylester 、 (+)-undec-1-en-5-ol 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 甲苯 为溶剂， 生成 Phthalic acid 1-((R)-1-but-3-enyl-heptyl) ester 2-pent-4-enyl ester
  参考文献：
  名称：

  Efficient phthalate-tethered ring-closing metathesis as a cross-coupling reaction

  摘要：

  An efficient method for cross-coupling using phthalate-tethered ring-closing metathesis was developed. Based on this method. the stereocontrolled syntheses of both (R,R)- and (S,R)-1-methoxypentadecane-2,9-diol (17, 20) were achieved from (R)-1-undecen-5-ol (4e) and (R)-1-methoxy-5-hexen-2-ol (13). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01649-5
• 作为产物：
  描述：

  庚醛 、 3-Butenylmagnesium bromide 在 12-冠醚-4 三异丙氧基氯化钛 、 Ti-TADDOLate 作用下， 生成 (S)-1-undecen-5-ol 、 (+)-undec-1-en-5-ol
  参考文献：
  名称：

  Ti-TADDOLate-catalyzed, highly enantioselective addition of alkyl- and aryl-titanum derivatives to aldehydes

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(01)90475-2

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.
• Efficient phthalate-tethered ring-closing metathesis as a cross-coupling reaction
  作者：Yasuharu Sakamoto、Masato Okazaki、Kazuyuki Miyamoto、Tadashi Nakata

  DOI：10.1016/s0040-4039(01)01649-5

  日期：2001.10

  An efficient method for cross-coupling using phthalate-tethered ring-closing metathesis was developed. Based on this method. the stereocontrolled syntheses of both (R,R)- and (S,R)-1-methoxypentadecane-2,9-diol (17, 20) were achieved from (R)-1-undecen-5-ol (4e) and (R)-1-methoxy-5-hexen-2-ol (13). (C) 2001 Elsevier Science Ltd. All rights reserved.