(R)-1-allyl-3-benzyloxy-2,6-piperidinedione | 1254985-48-2

• 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: (R)-1-allyl-3-benzyloxy-2,6-piperidinedione
• 英文别名: (3R)-3-phenylmethoxy-1-prop-2-enylpiperidine-2,6-dione
• CAS: 1254985-48-2
• 化学式: C₁₅H₁₇NO₃
• 分子量: 259.305
• InChiKey: INYOGCUCFHPOHI-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-1-allyl-3-benzyloxy-2,6-piperidinedione 在 盐酸 、 sodium tetrahydroborate 、 2,6-二叔丁基-4-甲基吡啶 、 草酰氯 、 三氟甲磺酸酐 、 二甲基亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 15.92h， 生成 (1S,5S,6R)-2-allyl-1-vinyl-2-azaspiro[bicyclo[3.3.1]nonane-4,2'-[1,3]dioxolan]-6-ol
  参考文献：
  名称：

  Enantioselective Total Syntheses of (−)-FR901483 and (+)-8-epi-FR901483

  摘要：

  The enantioselective total syntheses of the potent immunosuppressant FR901483 (1) and its 8-epimer (47) have been accomplished. Our approach features the use of building block 6 as the chiron, the application of the one-pot amide reductive bis-alkylation method to construct the chiral aza-quaternary center (dr = 9:1), regio- and diaster-eoselective intramolecular aldol reaction to build the bridged ring, and RCM to form the 3-pyrrolin-2-one ring.

  DOI：

  10.1021/jo302362b

文献信息

• A concise formal stereoselective total synthesis of (−)-swainsonine
  作者：Xiao-Gang Wang、Ai-E Wang、Pei-Qiang Huang

  DOI：10.1016/j.cclet.2013.12.003

  日期：2014.2

  A short formal stereoselective synthesis of (−)-swainsonine (1) is described. Our synthesis started with the versatile building block (R)-3-benzyloxyglutarimide 5. Through controlled regioselective reduction, Ley's-sulfone chemistry (N-α-sulfonylation and ZnCl2-catalyzed N-α-amidovinylation), an RCM reaction, and an amide reduction, the synthesis of unsaturated indolizidine (8R,8aS)-3 has been achieved

  描述了（-）-swainsonine（1）的简短形式立体选择性合成。我们的合成始于通用的结构单元（R）-3-苄氧基戊二酰亚胺5。通过控制区域选择性还原，莱氏砜化学反应（N - α-磺酰化和ZnCl 2催化的N - α-酰胺基乙烯基化），RCM反应和酰胺还原反应，可以合成不饱和吲哚并咪唑（8 R，8a S）-3已通过五个步骤实现。吲哚并咪唑（8 R，8a S）-3是合成（-）-swainsonine（1）的高级中间体。
• Studies towards an Enantioselective Total Synthesis of Sarain A: A Concise Asymmetric Construction of the Diazatricyclic Core
  作者：Rui-Feng Yang、Pei-Qiang Huang

  DOI：10.1002/chem.201001582

  日期：2010.9.10

  building block: A concise enantioselective synthesis of the diazatricyclic core of sarain A has been accomplished. The novel strategy relies upon the versatile chiral building block (R)‐1 (see scheme), and features a tandem Horner–Wadsworth–Emmons–aza‐Michael reaction, an intramolecular Michael reaction, and the diastereoconvergent formation of the third ring. Diazatricyclic core 2 possesses all of

  一个强大的手性结构单元：萨林A的二氮三环核心的简洁对映选择性合成已完成。新颖的策略依赖于通用的手性结构单元（R）-1（请参见方案），并具有串联的Horner-Wadsworth-Emmons-aza-Michael反应，分子内迈克尔反应和非对称会聚第三环的形成。二氮杂三环核2具有所有必要的功能，可以进一步加工成沙林A。
• Asymmetric syntheses of (8R,8aS)- and (8R,8aR)-8-hydroxy-5-indolizidinones: Two promising oxygenated indolizidine building blocks
  作者：HongKui Zhang、Xin Li、Huang Huang、PeiQiang Huang

  DOI：10.1007/s11426-011-4256-4

  日期：2011.5

  Starting from the oxygenated piperidine building block 20, two synthetic approaches to new building blocks (8R,8aS)- and (8R,8aR)-8-hydroxy-5-indolizidinones 19a/19b and 15a/15b have been developed, respectively. The first one is based on the trans-diastereoselective reductive alkylation (dr = 93:7), followed by a four-step procedure; and the second one called for the RCM reaction on the N,O-acetal derived from a vinylation, which was followed by a pyrrole formation, and a stereocontrolled cis-selective (dr = 91:9) catalytic hydrogenation. Reduction of the diastereomer 15a produced (8R,8aR)-8-indolizidinol (18).

  从含氧哌啶结构单元20开始，分别开发了两种合成新结构单元（8R,8aS）-和（8R,8aR）-8-羟基-5-吲哚嗪酮19a/19b和15a/15b的方法。第一种方法基于反式-非对映选择性还原烷基化（dr = 93:7），然后进行四步反应；第二种方法要求在乙烯化反应产生的N,O-乙缩醛上进行RCM反应，然后形成吡咯，最后进行立体选择性顺式（dr = 91:9）催化氢化。非对映异构体15a的还原反应生成（8R,8aR）-8-吲哚嗪醇（18）。
• A Formal Enantioselective Total Synthesis of FR901483
  作者：Hao-Hua Huo、Hong-Kui Zhang、Xiao-Er Xia、Pei-Qiang Huang

  DOI：10.1021/ol302165d

  日期：2012.9.21

  A formal enantioselective total synthesis of the potent immunosuppressant FR901483 (1) has been accomplished. Our approach features the use of chiron 6 as the starting material, the application of the one-pot amide reductive bisalkylation method to construct the chiral aza-quaternary center (dr = 9:1), regio- and diastereoselective intramolecular aldol reaction to build the bridged ring, and ring closing metathesis to form the 3-pyrrolin-2-one ring.
• Concise Asymmetric Total Synthesis of 9-<i>epi</i>-Sessilifoliamide J
  作者：Shi-Chuan Tuo、Jian-Liang Ye、Ai-E Wang、Su-Yu Huang、Pei-Qiang Huang

  DOI：10.1021/ol202140y

  日期：2011.10.7

  A 10-step asymmetric synthesis of 9-epi-sessilifoliamide J (20), together with sessilifoliamide J (6), has been accomplished from the key chiral building block 11 via a threo-selective vinylogous Mannich reaction and a Ley oxidation-SmI2-mediated coupling lactoniation. The absolute configuration of the natural sessilifoliamide J was established.