3-{2-[(4-methoxybenzyl)oxy]ethyl}oxetan-3-ylethanal | 1616253-45-2

• 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: 3-{2-[(4-methoxybenzyl)oxy]ethyl}oxetan-3-ylethanal
• CAS: 1616253-45-2
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: PWWWDYITPRZNDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.21
• 重原子数：
  19.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-{2-[(4-methoxybenzyl)oxy]ethyl}oxetan-3-ylethanal 在 咪唑 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 tert-butyl((1-(3-(2-((4-methoxybenzyl)oxy)ethyl)oxetan-3-yl)but-3-en-2-yl)oxy)dimethylsilane
  参考文献：
  名称：

  Concise synthesis and characterization of novel seco-steroids bearing a spiro-oxetane instead of a metabolically labile C3-hydroxy group

  摘要：

  Two novel stereoisomeric analogues of 1,25-dihydroxyvitamin D-3 bearing a spiro-oxetane at the C3 position of the A-ring have been designed and synthesized in a convergent manner. The absolute configuration at the Cl position of the synthesized compounds was determined by the circular dichroism exciton chirality method using the corresponding C1-allylic benzoates. The replacement of the C3-hydroxy group with a spiro-oxetane provided an advantageous conformational preference for the parent seco-steroids, which would facilitate the formation of a stable receptor complex. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.05.060
• 作为产物：
  描述：

  diethyl 2,2'-(oxetane-3,3-diyl)diacetate 在 lithium aluminium tetrahydride 、 草酰氯 、 四丁基碘化铵 、 sodium hydride 、 二甲基亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 、 mineral oil 为溶剂， 反应 25.42h， 生成 3-{2-[(4-methoxybenzyl)oxy]ethyl}oxetan-3-ylethanal
  参考文献：
  名称：

  Concise synthesis and characterization of novel seco-steroids bearing a spiro-oxetane instead of a metabolically labile C3-hydroxy group

  摘要：

  Two novel stereoisomeric analogues of 1,25-dihydroxyvitamin D-3 bearing a spiro-oxetane at the C3 position of the A-ring have been designed and synthesized in a convergent manner. The absolute configuration at the Cl position of the synthesized compounds was determined by the circular dichroism exciton chirality method using the corresponding C1-allylic benzoates. The replacement of the C3-hydroxy group with a spiro-oxetane provided an advantageous conformational preference for the parent seco-steroids, which would facilitate the formation of a stable receptor complex. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.05.060

文献信息

• The C4-functionalized 9,10-seco-5,7,10(19)-cholestatriene derivatives: Concise synthesis and characterization of novel vitamin D analogues with a four-membered heterocyclic ether
  作者：Tsutomu Suenega、Toshie Fujishima

  DOI：10.1016/j.tet.2018.02.001

  日期：2018.3

  Two novel stereoisomeric 9,10-seco-steroids (3a,b) bearing a spiro-oxetane at the C2 position of the A-ring with an unconventional C4-hydroxy group have been designed and synthesized by a convergent manner. The requisite A-ring enyne precursors (±)-9 were prepared in excellent yield from our reported aldehyde 4 according to a five-step procedure. The absolute configurations at the C4-hydroxy groups

  两种新型立体异构-9,10-开环-steroids（3A，3B）在轴承A环与非传统的C4-羟基的C2位置上的螺-杂环丁烷已设计并通过一个会聚的方式合成。根据我们的报告的醛4，按照五步程序，以极好的收率制备了必需的A环烯炔前体（±）-9。目标化合物的C4-羟基处的绝对构型（3a，b）是通过圆二色性（CD）激子手性法使用C4-烯丙基醇的相应苯甲酸酯确定的。使用牛胸腺VDR的初步生物学特性表明，在C2位掺入螺-氧杂环丁烷与C4位上的羟基结合会对VDR亲和力产生负面影响。