(S)-1-(4-methoxybenzyloxy)undec-5-yn-4-ol | 1189125-33-4

• 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-(4-methoxybenzyloxy)undec-5-yn-4-ol
• 英文别名: (4S)-1-[(4-methoxyphenyl)methoxy]undec-5-yn-4-ol
• CAS: 1189125-33-4
• 化学式: C₁₉H₂₈O₃
• 分子量: 304.43
• InChiKey: VLIZLJSCKXCCHZ-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-吡啶甲酸 、 (S)-1-(4-methoxybenzyloxy)undec-5-yn-4-ol 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以93%的产率得到(S)-1-(4-methoxybenzyloxy)undec-5-yn-4-yl pyridine-2-carboxylate
  参考文献：
  名称：

  Formation of Chiral C(sp³)−C(sp) Bond by Allylic Substitution of Secondary Allylic Picolinates and Alkynyl Copper Reagents

  摘要：

  To establish allylic substitution of secondary allylic alcohol derivatives with alkynyl copper reagents, allylic esters bearing the (2-pyridine)CO2-, (2-pyrazine)CO2-, (EtO)(2)PO2-, C6F5CO2-, o-(Ph2P)-C6H4CO2-, MeOCO2-, or AcO-group were examined. First, picolinate (R-1 = Me, R-2 = CH2OPMB) was subjected to reaction with (TMS-C C)(2)CuLi center dot LiBr at 0 degrees C. Although no substitution took place, MgBr, (3 equiv) was found to promote the reaction to produce the anti S(N)2' product in 93% yield with 94% regioselectivity and 99% chirality transfer. In contrast, substitution of the other esters with the copper reagent in the presence of MgBr, were less reactive ((2-pyrazin)CO2-) or marginally reactive (other cases). Generality of the substitution using picolinates was established with five picolinates (R-1 = Me, Ph(CH2)(2), PMBO(CH2)(3); R-2 = Me, CH2OPMB, CH2OTBS, C5H11, c-C6H11) and seven alkynyl copper reagents (R-3 = TMS, Ph, p-TBSOC6H4, p- and o-MeOC6H4, P-MeC6H4, p-FC6H4), furnishing anti S(N)2' products in 61-93% yields with high regioselectivity (usually > 90%) and high chirality transfer (usually > 95%). In addition, transformation of the products was briefly studied.

  DOI：

  10.1021/jo901728b
• 作为产物：
  描述：

  1-(4-methoxybenzyloxy)undec-5-yn-4-one 在 Noyori's catalyst 、 异丙醇 作用下， 以84%的产率得到(S)-1-(4-methoxybenzyloxy)undec-5-yn-4-ol
  参考文献：
  名称：

  Formation of Chiral C(sp³)−C(sp) Bond by Allylic Substitution of Secondary Allylic Picolinates and Alkynyl Copper Reagents

  摘要：

  To establish allylic substitution of secondary allylic alcohol derivatives with alkynyl copper reagents, allylic esters bearing the (2-pyridine)CO2-, (2-pyrazine)CO2-, (EtO)(2)PO2-, C6F5CO2-, o-(Ph2P)-C6H4CO2-, MeOCO2-, or AcO-group were examined. First, picolinate (R-1 = Me, R-2 = CH2OPMB) was subjected to reaction with (TMS-C C)(2)CuLi center dot LiBr at 0 degrees C. Although no substitution took place, MgBr, (3 equiv) was found to promote the reaction to produce the anti S(N)2' product in 93% yield with 94% regioselectivity and 99% chirality transfer. In contrast, substitution of the other esters with the copper reagent in the presence of MgBr, were less reactive ((2-pyrazin)CO2-) or marginally reactive (other cases). Generality of the substitution using picolinates was established with five picolinates (R-1 = Me, Ph(CH2)(2), PMBO(CH2)(3); R-2 = Me, CH2OPMB, CH2OTBS, C5H11, c-C6H11) and seven alkynyl copper reagents (R-3 = TMS, Ph, p-TBSOC6H4, p- and o-MeOC6H4, P-MeC6H4, p-FC6H4), furnishing anti S(N)2' products in 61-93% yields with high regioselectivity (usually > 90%) and high chirality transfer (usually > 95%). In addition, transformation of the products was briefly studied.

  DOI：

  10.1021/jo901728b

文献信息

• Formation of Chiral C(sp³)−C(sp) Bond by Allylic Substitution of Secondary Allylic Picolinates and Alkynyl Copper Reagents
  作者：Yohei Kiyotsuka、Yuichi Kobayashi

  DOI：10.1021/jo901728b

  日期：2009.10.2

  To establish allylic substitution of secondary allylic alcohol derivatives with alkynyl copper reagents, allylic esters bearing the (2-pyridine)CO2-, (2-pyrazine)CO2-, (EtO)(2)PO2-, C6F5CO2-, o-(Ph2P)-C6H4CO2-, MeOCO2-, or AcO-group were examined. First, picolinate (R-1 = Me, R-2 = CH2OPMB) was subjected to reaction with (TMS-C C)(2)CuLi center dot LiBr at 0 degrees C. Although no substitution took place, MgBr, (3 equiv) was found to promote the reaction to produce the anti S(N)2' product in 93% yield with 94% regioselectivity and 99% chirality transfer. In contrast, substitution of the other esters with the copper reagent in the presence of MgBr, were less reactive ((2-pyrazin)CO2-) or marginally reactive (other cases). Generality of the substitution using picolinates was established with five picolinates (R-1 = Me, Ph(CH2)(2), PMBO(CH2)(3); R-2 = Me, CH2OPMB, CH2OTBS, C5H11, c-C6H11) and seven alkynyl copper reagents (R-3 = TMS, Ph, p-TBSOC6H4, p- and o-MeOC6H4, P-MeC6H4, p-FC6H4), furnishing anti S(N)2' products in 61-93% yields with high regioselectivity (usually > 90%) and high chirality transfer (usually > 95%). In addition, transformation of the products was briefly studied.