N-methoxy-N-methyl-2-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)acetamide | 195702-97-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-methoxy-N-methyl-2-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)acetamide
• 英文别名: (1S,4aS,8aS)-N-methoxy-N-methyl-1-(2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8-octahydronaphthalenyl)acetamide；2-[(1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-N-methoxy-N-methylacetamide
• CAS: 195702-97-7
• 化学式: C₁₈H₃₁NO₂
• 分子量: 293.45
• InChiKey: BWWVJBCYENEWKA-RLFYNMQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-methoxy-N-methyl-2-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)acetamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以87%的产率得到2-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)acetaldehyde
  参考文献：
  名称：

  肌动菜红酮的正式全合成和Labda-7,13-（E）-dien -15-ol的不对称合成

  摘要：

  依靠催化方法以简明的方式报道了放线菌酮的聚酮化合物和萜类化合物片段的合成。最小化使用保护基和氧化还原反应使得可以以20个步骤（对于LLS为11个步骤）合成肌动龙酮的碳主链。还公开了labda-7，13-（E）-dien -15-ol的不对称合成。

  DOI：

  10.1021/acs.orglett.7b01287
• 作为产物：
  描述：

  methyl 2-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)acetate 在 lithium hydroxide 、 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.0h， 生成 N-methoxy-N-methyl-2-((1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)acetamide
  参考文献：
  名称：

  Synthesis and phosphatase inhibitory activity of analogs of sulfircin

  摘要：

  Analogs of sulfircin (1) were synthesized and tested for inhibitory activity against a panel of phosphatases. We attempted to optimize the potency and selectivity of sulfircin for Cdc25A by modifying three structural areas of the molecule. An anionic group is required for potency and malonate was found to be an effective substitute for sulfate. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00357-0

文献信息

• Formal Total Synthesis of Actinoranone: Synthesis Approaches and Cytotoxic Studies
  作者：Luiz F. T. Novaes、Kaliandra de Almeida Gonçalves、Daniela B. B. Trivella、Julio C. Pastre

  DOI：10.1021/acs.joc.8b00514

  日期：2018.5.4

  toward the total synthesis of actinoranone. Our synthesis strategies rely on a convergent route to connect the terpenoid and polyketide fragments, employing catalysis and powerful classical reactions for the assembly of these key fragments. A new transformation was disclosed during this work, a domino ring-opening and esterification. Initial cytotoxic studies for the selected synthesis intermediates are

  本文介绍了我们努力合成肌动龙酮的努力。我们的合成策略依赖于收敛路线来连接萜类化合物和聚酮化合物片段，并利用催化作用和强大的经典反应来组装这些关键片段。在这项工作中公开了一种新的转变，即多米诺环的开环和酯化。还介绍了所选合成中间体的初步细胞毒性研究。
• Lewis Acid‐Catalyzed Stereoselective α‐Addition of Chiral Aldehydes to Cyclic Dienol Silanes: Aqueous Synthesis of Chiral Butenolides
  作者：Anna Adamkiewicz、Izabela Węglarz、Aleksandra Butkiewicz、Marta Woyciechowska、Jacek Mlynarski

  DOI：10.1002/adsc.201901218

  日期：2020.2.6

  stereoselective α‐addition to cyclic dienol silanes has rarely been exploited, in contrast to the well‐studied γ‐addition of conjugated butenolides. In this study, an unprecedent catalytic Mukaiyama aldol α‐addition of 2‐trimetylsiloxy furan to optically pure aldehydes in water‐containing solvents is reported. The synthetic utility of this concept was demonstrated in the efficient synthesis of six bioactive natural

  与对丁二酸内酯共轭的γ-加成研究相比，对环二烯醇硅烷的立体选择性α-加成很少被利用。在这项研究中，报道了在含水溶剂中空前催化2-三甲硅氧基甲氧基呋喃的Mukaiyama aldolα-加成到光学纯醛中的现象。该概念的合成效用在六种生物活性天然产物的有效合成中得到了证明：维特索利德D，姜黄素肌醇C，短毛菌素，海胆碱C，（+）- Coronarin E和（E）-labda‐7,11,13‐trien‐ 16,15-橄榄。
• An Approach to Furolabdanes and Their Photooxidation Derivatives from <i>R</i>-(+)<i>-</i>Sclareolide
  作者：María C. de la Torre、Isabel García、Miguel A. Sierra

  DOI：10.1021/np010590u

  日期：2002.5.1

  A synthetic route to furolabdanes from commercially available R-(+)-selareolide is reported, with the specific aim of preparing (12R and 12S,15xi)-12,15-dihydroxylabda-7,13-dien-16,15-olides (3 and 5) and (12R and 12S,16xi)-12,16-dihydroxylabda-7,13-dien-15,16-olides (4 and 6). The key points of our approach are the use of Weinreb's amide 11 to join the furan ring to the terpenic unit. Photooxidation of the furan moiety of compounds 15 and 16, and of their acetates 19 and 20, has been used to built the hydroxybutenolide fragment. In this way the four possible isomers at the butenolide moiety, compounds 3-6, and their C-12 acetyl derivatives 21-24 have been obtained. On the basis of comparison of the spectral data (H-1 NMR) of the synthetic peracetates 25-28 (derived from 21-24) with the reported data for the peracetate 2 (derived from the natural product 1), the relative configuration at carbon C-12 of the natural product has been corrected. Furthermore, the absolute configuration of the natural product 1, considered to belong to the enantio-series, has to be changed to the normal-series on the basis of the optical rotation obtained for the synthetic derivative.
• Straightforward synthesis of the strong ambergris odorant γ-bicyclohomofarnesal and its endo-isomer from R-(+)-sclareolide
  作者：Marı́a C. de la Torre、Isabel Garcı́a、Miguel A. Sierra

  DOI：10.1016/s0040-4039(02)01392-8

  日期：2002.9

  gamma-Bicyclohomofarnesal 1 and its endo isomer 5 were prepared in 47 and 26% overall yields, respectively, from commercial R-(+)-sclareolide (7), in a three-step sequence. The synthetic procedure involves the preparation of Weinreb's amide 9, dehydration of tertiary alcohol to form compounds 10 and 11, chromatographic separation and reduction with LiAlH4. This approach is simple and can compete with the syntheses previously reported for the preparation of these important compounds, both in overall yields and in the number of synthetic steps. (C) 2002 Elsevier Science Ltd. All rights reserved.