7-(2-hexyl-1,3-dioxolan-2-yl)heptanal | 172330-97-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-(2-hexyl-1,3-dioxolan-2-yl)heptanal
• CAS: 172330-97-1
• 化学式: C₁₆H₃₀O₃
• 分子量: 270.412
• InChiKey: NLGJHVCSUUMMOC-UHFFFAOYSA-N

物化性质

• 沸点：
  359.5±17.0 °C(Predicted)
• 密度：
  0.931±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-(2-hexyl-1,3-dioxolan-2-yl)heptanal 在 甲醇 、 sodium hydroxide 、 sodium tetrahydroborate 、 N-氯代丁二酰亚胺 、 氯化亚砜 、 三氟化硼乙醚 、 双(三甲基硅烷基)氨基钾 、 silver nitrate 、 二苯二硫醚 、 三氟乙酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 苯 为溶剂， 生成 Mycestericin E
  参考文献：
  名称：

  Determination of the absolute configurations and total synthesis of new immunosuppressants, mycestericins E and G

  摘要：

  DOI：

  10.1016/0040-4039(95)01823-z
• 作为产物：
  描述：

  14-Benzyloxy-tetradecan-7-ol 在 palladium on activated charcoal 草酰氯 、 氢气 、 对甲苯磺酸 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 生成 7-(2-hexyl-1,3-dioxolan-2-yl)heptanal
  参考文献：
  名称：

  Determination of the absolute configurations and total synthesis of new immunosuppressants, mycestericins E and G

  摘要：

  DOI：

  10.1016/0040-4039(95)01823-z

文献信息

• Total Synthesis of the Immunosuppressants Myriocin and 2-<i>epi</i>-Myriocin
  作者：Matthew C. Jones、Stephen P. Marsden

  DOI：10.1021/ol801709c

  日期：2008.9.18

  Total syntheses of the natural immunosuppressant myriocin (1) and the equipotent unnatural analogue 2-epi-myriocin (in protected form) have been achieved through a common strategy. The key transformations are the efficient synthesis of a quaternary (E)-vinylglycine by asymmetric deconjugative alkylation of a dehydroamino acid and an unusually highly diastereoselective dihydroxylation of the vinylglycine

  天然免疫抑制剂myriocin（1）和等价的非天然类似物2-epio-myriocin（处于保护状态）的总合成已通过一种常见策略实现。关键的转变是通过脱氢氨基酸的不对称去共轭烷基化和乙烯基甘氨酸烯烃的异常非对映选择性二羟基化来有效合成季（E）-乙烯基甘氨酸。
• A stereoselective total synthesis of the HCl salts of mycestericins F, G and ent-F
  作者：Miroslava Martinková、Jozef Gonda、Alena Uhríková、Jana Špaková Raschmanová、Mária Vilková、Beáta Oroszová

  DOI：10.1016/j.tetasy.2012.12.003

  日期：2013.2

  The total synthesis of the HCl salts of two natural sphingolipid-related amino acid derivatives, mycestericins F 4 and G 5 together with unnatural ent-4 center dot HCl, starting from the four crucial scaffolds 6, 8, 9, 11 and utilizing the Wittig reaction to build the C-20 backbone, has been achieved. The selection of selective functional group interconversions accompanied with suitable protection-deprotection protocols in the coupling products 20 and 34 gave the desired structures. (C) 2012 Elsevier Ltd. All rights reserved.
• An Efficient Enantioselective Synthesis of (2<i>R</i>)-Hydroxymethyl Glutamic Acid and an Approach to the (2<i>R</i>)-Hydroxymethyl-Substituted Sphingofungins
  作者：Christopher J. Hayes、Daniel M. Bradley、Nicholas M. Thomson

  DOI：10.1021/jo052408q

  日期：2006.3.31

  We have developed a short enantioselective synthesis of (2R)-hydroxymethyl glutamic acid (HMG) starting from Garner's aldehyde using an alkylidene carbene 1,5-CH insertion as a method to construct the quaternary stereocenter. A variety of conditions were examined for the oxidative cleavage of the key cyclopentene intermediate and we found that RuCl3/NaIO4 led directly to the desired amino bis-acid product. We were also able to show that oxidative cleavage of the cyclopentene 1,5-CH insertion product could be used to produce the amino acid-containing skeleton of the sphingofungin family of natural products.
• Stereocontrolled total synthesis of (−)-myriocin
  作者：Makoto Inai、Toshihiro Goto、Takumi Furuta、Toshiyuki Wakimoto、Toshiyuki Kan

  DOI：10.1016/j.tetasy.2008.12.020

  日期：2008.12

  The stereocontrolled total synthesis of (-)-myriocin 1 is reported. Optically active epoxide 9 was converted from symmetrical cyclohexadiene 8, utilizing an enzymatic kinetic resolution. The three sequential stereogenic centers of 1 were constructed by a regioselective epoxide-opening reaction and a Hofmann rearrangement. Elongation of the side chain was efficiently accomplished by the Julia-Kocienski reaction. Published by Elsevier Ltd.