(R)-4-((4-methoxybenzyl)oxy)-2-methylbutan-1-ol | 727411-51-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-4-((4-methoxybenzyl)oxy)-2-methylbutan-1-ol
• 英文别名: (2R)-4-[(4-methoxybenzyl)oxy]-2-methyl-1-butanol；(2R)-4-[(4-methoxyphenyl)methoxy]-2-methylbutan-1-ol
• CAS: 727411-51-0
• 化学式: C₁₃H₂₀O₃
• 分子量: 224.3
• InChiKey: XWIPBWCLWRPHSZ-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 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：

  (R)-4-((4-methoxybenzyl)oxy)-2-methylbutan-1-ol 在 草酰氯 、 18-冠醚-6 、 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 0.25h， 生成 (Z)-(R)-2-Ethyl-6-(4-methoxy-benzyloxy)-4-methyl-hex-2-en-1-ol
  参考文献：
  名称：

  Participation of the conjugated diene part for potent cytotoxicity of callystatin A, a spongean polyketide

  摘要：

  5-epi, 10-epi, 8-Deethyl, and 10-demethyl analogues of callystatin A, a potent cytotoxic spongean polyketide, were synthesized to elucidate structure-requirement for cytotoxic potency. Inversion of the asymmetric center at C-10 in callystatin A minimally affected the activity, while lack of the 10-methyl group in callystatin A decreased cytotoxicity. In addition, the C-5 epimer and the 8-deethyl analogue of callystatin A showed weaker cytotoxicity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00199-1
• 作为产物：
  描述：

  (3R)-3-Methyl-4-tert-butyldimethylsilyloxybutanonitrile 在 甲醇 、 sodium tetrahydroborate 、 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 55.0h， 生成 (R)-4-((4-methoxybenzyl)oxy)-2-methylbutan-1-ol
  参考文献：
  名称：

  Scyphosstatin疏水侧链的立体选择性合成

  摘要：

  scyphosstatin的疏水侧链是通过聚合合成途径合成的。关键反应是内消旋二醇的酶促不对称乙酰化，通过 Negishi 偶联构建 C12'-C13' 三取代的 E-烯烃部分，以及构建 (2'E,4'E ,E,6'E)霍纳-沃兹沃思-埃蒙斯烯化的-三烯部分。

  DOI：

  10.1071/ch03298

文献信息

• Synthesis of Enantiopure Bicyclic α,α-Disubstituted Spirolactams via Asymmetric Birch Reductive Alkylation
  作者：Stéphanie M. Guéret、Patrick D. O’Connor、Margaret A. Brimble

  DOI：10.1021/ol8029017

  日期：2009.2.19

  The synthesis of enantiopure bicyclic α,α-disubstituted spirolactams is described using a diastereoselective Birch reductive alkylation as the key step. Hydrogenation of the resultant alkylated cyclohexadienes followed by intramolecular cyclization provides access to enantiopure 8-azaspiro[5.6]dodecan-7-ones.

  以非对映选择性的桦木还原烷基化为关键步骤描述了对映体纯的双环α，α-二取代螺内酰胺的合成。氢化所得的烷基化环己二烯，然后进行分子内环化，可提供对映体纯的8-氮杂螺并[5.6]十二烷基-7-酮。
• Synthetic Studies on Amphirionin-5: Stereochemical Assignment/Reassignment of the C1–C9 Portion through Stereodivergent Synthesis
  作者：Moemi Kanto、Makoto Sasaki

  DOI：10.1021/acs.orglett.5b03346

  日期：2016.1.4

  Synthesis of four diastereomers of the C1–C12 fragment of amphirionin-5 has been achieved in a convergent and stereodivergent manner. Detailed comparison of the 1H and 13C NMR data of each compound with those reported for the natural product led to not only the stereochemical assignment of the relative configuration of the C4/C5 stereogenic centers but also reassignment of the proposed relative configuration

  amphirionin-5的C1-C12片段的四种非对映异构体的合成已经以收敛和立体发散的方式实现。每种化合物的1 H和13 C NMR数据与天然产物的详细比较，不仅导致立体化学指定C4 / C5立体异构中心的相对构型，而且还重新分配了拟议的C9 / C5相对构型。 amphirionin-5。
• Stereodivergent Synthesis and Configurational Assignment of the C1–C15 Segment of Amphirionin-5
  作者：Moemi Kanto、Sota Sato、Masashi Tsuda、Makoto Sasaki

  DOI：10.1021/acs.joc.6b01700

  日期：2016.10.7

  The relative configuration of the C3–C12 portion of amphirionin-5, a novel marine polyketide with potent cell proliferation-promoting activity, was established by the stereodivergent synthesis of six diastereomeric model compounds and comparison of their NMR spectroscopic data with those reported for the natural product. This study led to the elucidation of the relative configuration between C4/C5

  amphirionin-5（一种具有有效的细胞增殖促进活性的新型海洋聚酮化合物）C3–C12部分的相对构型是通过六种非对映体模型化合物的立体发散合成并将其NMR光谱数据与报道的天然非对映化合物进行比较而建立的产品。这项研究导致阐明了C4 / C5和C9 / C12之间的相对构型，并重新提出了拟南芥5的C9位置的拟议构型。
• Diastereoselective and Branched-Aldehyde-Selective Tandem Hydroformylation–Hemiaminal Formation: Synthesis of Functionalized Piperidines and Amino Alcohols
  作者：Rachael Pittaway、José A. Fuentes、Matthew L. Clarke

  DOI：10.1021/acs.orglett.7b01049

  日期：2017.6.2

  developed for the synthesis of chiral functionalized piperidines, with very good diastereoselectivity and branched regioselectivity using Rh/(S,S,S)-BOBPHOS catalysts. Tandem hydroformylation–hemiacetal formation also proceeds with good diastereoselectivity (88:12), with the hemiacetal product being hydrogenated with retention of stereochemistry to give a chiral intermediate used in the synthesis of the new

  从容易获得的烯丙基甘氨酸开始，已开发出串联加氢甲酰化-半胱氨酸形成反应，用于合成手性官能化哌啶，使用Rh /（S，S，S）-BOBPHOS催化剂具有非常好的非对映选择性和支链区域选择性。串联加氢甲酰化-半缩醛的形成也具有良好的非对映选择性（88:12），半缩醛产物被氢化并保留了立体化学，从而提供了一种手性中间体，用于合成新的抗生素奈诺沙星。
• Participation of the conjugated diene part for potent cytotoxicity of callystatin A, a spongean polyketide
  作者：Nobutoshi Murakami、Masanori Sugimoto、Tatsuo Nakajima、Motoyuki Kawanishi、Yasuhiro Tsutsui、Motomasa Kobayashi

  DOI：10.1016/s0968-0896(00)00199-1

  日期：2000.11

  5-epi, 10-epi, 8-Deethyl, and 10-demethyl analogues of callystatin A, a potent cytotoxic spongean polyketide, were synthesized to elucidate structure-requirement for cytotoxic potency. Inversion of the asymmetric center at C-10 in callystatin A minimally affected the activity, while lack of the 10-methyl group in callystatin A decreased cytotoxicity. In addition, the C-5 epimer and the 8-deethyl analogue of callystatin A showed weaker cytotoxicity. (C) 2000 Elsevier Science Ltd. All rights reserved.